(1S,2R,3S)-2-benzyloxy-1-(t-butyldimethylsilyloxy)-1-phenyl-3,4-butanediol

Base Information

Chemical Name:(1S,2R,3S)-2-benzyloxy-1-(t-butyldimethylsilyloxy)-1-phenyl-3,4-butanediol
CAS No.:220384-88-3
Molecular Formula:C₂₃H₃₄O₄Si
Molecular Weight:402.606
Hs Code.:

Synonyms:(1S,2R,3S)-2-benzyloxy-1-(t-butyldimethylsilyloxy)-1-phenyl-3,4-butanediol

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Chemical Property of (1S,2R,3S)-2-benzyloxy-1-(t-butyldimethylsilyloxy)-1-phenyl-3,4-butanediol

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Technology Process of (1S,2R,3S)-2-benzyloxy-1-(t-butyldimethylsilyloxy)-1-phenyl-3,4-butanediol

There total 5 articles about (1S,2R,3S)-2-benzyloxy-1-(t-butyldimethylsilyloxy)-1-phenyl-3,4-butanediol 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: 88.0%

: 220384-87-2
{(4S,5R)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2-phenyl-[1,3]dioxolan-4-yl}-methanol

: 220384-88-3
(1S,2R,3S)-2-benzyloxy-1-(t-butyldimethylsilyloxy)-1-phenyl-3,4-butanediol

Guidance literature:: {(4S,5R)-5-[(S)-(tert-Butyl-dimethyl-silanyloxy)-phenyl-methyl]-2-phenyl-[1,3]dioxolan-4-yl}-methanol; With dimethylsulfide borane complex; In dichloromethane; at 0 - 20 ℃; for 1h;

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 0.333333h;
DOI:10.1016/S0040-4020(99)00794-2

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 220384-88-3
(1S,2R,3S)-2-benzyloxy-1-(t-butyldimethylsilyloxy)-1-phenyl-3,4-butanediol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 95 percent / camphorsulfonic acid / benzene / 1 h / Heating

2.1: 99 percent / LiAlH₄ / diethyl ether / 0.08 h / 0 °C

3.1: BH₃*Me₂S / CH₂Cl₂ / 1 h / 0 - 20 °C

3.2: 88 percent / BF₃*Et₂O / CH₂Cl₂ / 0.33 h / 0 °C

With lithium aluminium tetrahydride; dimethylsulfide borane complex; camphor-10-sulfonic acid; In diethyl ether; dichloromethane; benzene; 1.1: Cyclization / 2.1: Reduction / 3.1: Ring cleavage / 3.2: Ring cleavage;
DOI:10.1016/S0040-4020(99)00794-2

Reference yield:

: (E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-4-phenyl-but-2-enoic acid ethyl ester

: 220384-88-3
(1S,2R,3S)-2-benzyloxy-1-(t-butyldimethylsilyloxy)-1-phenyl-3,4-butanediol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 97 percent / AD-mix-β; CH3SO2NH2 / 2-methyl-propan-2-ol; H2O / 36 h / 20 °C

2.1: 95 percent / camphorsulfonic acid / benzene / 1 h / Heating

3.1: 99 percent / LiAlH₄ / diethyl ether / 0.08 h / 0 °C

4.1: BH₃*Me₂S / CH₂Cl₂ / 1 h / 0 - 20 °C

4.2: 88 percent / BF₃*Et₂O / CH₂Cl₂ / 0.33 h / 0 °C

With lithium aluminium tetrahydride; methanesulfonamide; dimethylsulfide borane complex; AD-mix-β; camphor-10-sulfonic acid; In diethyl ether; dichloromethane; water; tert-butyl alcohol; benzene; 1.1: hydroxylation / 2.1: Cyclization / 3.1: Reduction / 4.1: Ring cleavage / 4.2: Ring cleavage;
DOI:10.1016/S0040-4020(99)00794-2