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

Base Information

Chemical Name:(1S,2R,3R)-2-benzyloxy-4-t-butylcarbonyloxy-1-t-butyldimethylsilyloxy-4-phenyl-3-butanol
CAS No.:220384-90-7
Molecular Formula:C₂₈H₄₂O₅Si
Molecular Weight:486.724
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 6 articles about (1S,2R,3R)-2-benzyloxy-4-t-butylcarbonyloxy-1-t-butyldimethylsilyloxy-4-phenyl-3-butanol 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: 97.0%

: 3282-30-2
pivaloyl chloride

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

: 220384-90-7
(1S,2R,3R)-2-benzyloxy-4-t-butylcarbonyloxy-1-t-butyldimethylsilyloxy-4-phenyl-3-butanol

Guidance literature:: With dmap; In dichloromethane; at 20 ℃; for 0.25h;
DOI:10.1016/S0040-4020(99)00794-2

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 220384-90-7
(1S,2R,3R)-2-benzyloxy-4-t-butylcarbonyloxy-1-t-butyldimethylsilyloxy-4-phenyl-3-butanol

Guidance literature:: Multi-step reaction with 4 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

4.1: 97 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 0.25 h / 20 °C

With dmap; 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 / 4.1: Acylation;
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

: 220384-90-7
(1S,2R,3R)-2-benzyloxy-4-t-butylcarbonyloxy-1-t-butyldimethylsilyloxy-4-phenyl-3-butanol

Guidance literature:: Multi-step reaction with 5 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

5.1: 97 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 0.25 h / 20 °C

With dmap; 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 / 5.1: Acylation;
DOI:10.1016/S0040-4020(99)00794-2