Toluene-4-sulfonic acid (2R,3S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-phenyl-butyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (2R,3S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-phenyl-butyl ester
CAS No.:185335-97-1
Molecular Formula:C₂₃H₃₄O₆SSi
Molecular Weight:466.671
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (2R,3S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-phenyl-butyl ester

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Chemical Property of Toluene-4-sulfonic acid (2R,3S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-phenyl-butyl ester

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Technology Process of Toluene-4-sulfonic acid (2R,3S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-phenyl-butyl ester

There total 5 articles about Toluene-4-sulfonic acid (2R,3S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-phenyl-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 85.0%

: 98-59-9
p-toluenesulfonyl chloride

: 185335-96-0
(2R,3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-4-phenyl-butane-1,2,3-triol

: 185335-97-1
Toluene-4-sulfonic acid (2R,3S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-phenyl-butyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at -20 ℃;
DOI:10.1016/0957-4166(96)00431-4

Reference yield:

: 130115-07-0
(R)-2-(t-butyldimethylsilyloxy)-2-phenylacetaldehyde

: 185335-97-1
Toluene-4-sulfonic acid (2R,3S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-phenyl-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 86 percent / toluene / 0.5 h / Heating

2: 85 percent / N-methyl morpholine N-oxide hydrate, OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / Ambient temperature

3: 98 percent / LiBH₄ / tetrahydrofuran / 0.33 h / Ambient temperature

4: 85 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / -20 °C

With dmap; osmium(VIII) oxide; lithium borohydride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1016/0957-4166(96)00431-4

Reference yield:

: 153293-97-1
ethyl (R)-2-(tert-butyldimethylsilyloxy)-2-phenylacetate

: 185335-97-1
Toluene-4-sulfonic acid (2R,3S,4R)-4-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-phenyl-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: DIBAL-H / diethyl ether; hexane / 0.33 h / -78 °C

2: 86 percent / toluene / 0.5 h / Heating

3: 85 percent / N-methyl morpholine N-oxide hydrate, OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / Ambient temperature

4: 98 percent / LiBH₄ / tetrahydrofuran / 0.33 h / Ambient temperature

5: 85 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / -20 °C

With dmap; osmium(VIII) oxide; lithium borohydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetone; toluene; tert-butyl alcohol;
DOI:10.1016/0957-4166(96)00431-4