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Sku SC15-0067_5_G
US-Strem
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Product Information

Product Name
(S)-(+)-5,5'-Bisdi(3,5-di-t-butyl-4-methoxyphenyl)phosphino-4,4'-bi-1,3-benzodioxole, min. 98% (S)-(+)-DTBM-SEGPHOS
Brand Name
US-Strem
Product Number
15-0067
CAS
210169-40-7
Certificate of Analysis (COA)​
COA not found

General Information

PubChem CID
11194192
IUPAC Name
4-5-bis(3,5-ditert-butyl-4-methoxyphenyl)phosphanyl-1,3-benzodioxol-4-yl-1,3-benzodioxol-5-yl-bis(3,5-ditert-butyl-4-methoxyphenyl)phosphane
InChI Key
ZNORAFJUESSLTM-UHFFFAOYSA-N
SMILES
CC(C)(C)C1=CC(=CC(=C1OC)C(C)(C)C)P(C2=C(C3=C(C=C2)OCO3)C4=C(C=CC5=C4OCO5)P(C6=CC(=C(C(=C6)C(C)(C)C)OC)C(C)(C)C)C7=CC(=C(C(=C7)C(C)(C)C)OC)C(C)(C)C)C8=CC(=C(C(=C8)C(C)(C)C)OC)C(C)(C)C

Application

Technical Notes:
1. Biaryl bisphosphine ligand with narrow dihedral angle. The DTBM SEGPHOS® ligand, as the
ruthenium complex, gives superior enantioselectivity and diaste reoselectivity through dynamic kinetic resolution in the asymmetric hydrogenation of a-substituted-ß-ketoesters useful in the synthesis of carbapenum antibiotics.
2. With rhodium, preferential enantioselective hydrogenation of more reactive olefin of extended enone structure .
3.Rhodium catalyzed chemo-, regio, and entantioselective 2 + 2 + 2 cycloaddition of alkynes with isocyanates .
4.With copper, enantioselective cross Aldol-type reaction of acetonitrile.4
5.With copper, enantioselective vinylsilane alkenylation of aldehydes .5
6.Gold carbene mediated stereoselective cyclopropanation of propargyl esters.
7.With copper, enantioselective 1,2 -reduction of ketones, and 1 ,4-reduction of a a,ß-usaturatedesters.
8.With copper, catalytic enantioselective Mannich-type reaction.
9.Enantioselective fluorination of b ß-keto esters, tert- butoxycarbonyl lactones and lactmes with Sodeoka's Pd-aqua complex and a fluorinating reagent.
10.Rh-catalyzed intramolecular olefin or carbonyl hydroacylation. 10
11.Pd-catalyzed y-arylation of ß,y-unsaturated ketones.
12Involved in numerous conjugate alkynylation, and ring-opening alkynylation of
azabenzonorbornadienes.
13.Involved in asymmetric hydroamination of bicyclic alkenes/die nes, 13a diamination of conjugated dienes,sb and hydroalkoxylation/hydrosulfenylation of allenes.se
14.Used in cycloaddition reactions such as 1,3-dipolar cycloaddition of azomethine ylides, and Au-catalyzed 2 +2 cycoaddition of allenes.
15.Asymmetric conjugate addition of nitroalkanes to a,ß-usaturated thioamides.
16.Asymmetric synthesis of isothiazoles through Cu catalyzed conjugate addition of allyl cyanide to a,ß-usaturated thioamides .
17.Asymmetric Ag-catalyzed cycloadditions."
18.Rhodium-catalyzed c c bond cleavage to generate acyclic, asymmetric quaternary centers.
19.Iridium-catalyzed intermolecular hydroamidation of olefins .
20.Iridium-catalyzed intermolecular hydroamidation of olefins.
21.CuH-catalyzed asymmetric hydroamination of olefins.

References Data Source From Pubchem

Enolates as Nucleophiles

Publication Name: Science of Synthesis
Publication Date: 2026

Synthesis of chiral phosphine derivatives through a copper(I)-catalyzed desymmetric SNAr reaction

Publication Name: Science China Chemistry
Publication Date: 2025-01-03
DOI: 10.1007/s11426-024-2435-0

A guide for asymmetric synthesis of morphine alkaloids

Publication Name: Medicinal Chemistry Research
Publication Date: 2024-11-21
DOI: 10.1007/s00044-024-03350-9

The current utility and future potential of multiborylated alkanes

Publication Name: Nature reviews. Chemistry
Publication Date: 2024-09-26
DOI: 10.1038/s41570-024-00650-x

Copper-catalysed asymmetric hydroboration of alkenes with 1,2-benzazaborines to access chiral naphthalene isosteres

Publication Name: Nature Chemistry
Publication Date: 2024-04-08
DOI: 10.1038/s41557-024-01505-0