ethyl (2R,3R,4S)-4-(t-butyldimethylsilyloxy)-2,3-dihydroxy-4-phenylbutanoate

Base Information

Chemical Name:ethyl (2R,3R,4S)-4-(t-butyldimethylsilyloxy)-2,3-dihydroxy-4-phenylbutanoate
CAS No.:220384-85-0
Molecular Formula:C₁₈H₃₀O₅Si
Molecular Weight:354.519
Hs Code.:

Synonyms:ethyl (2R,3R,4S)-4-(t-butyldimethylsilyloxy)-2,3-dihydroxy-4-phenylbutanoate

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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 ethyl (2R,3R,4S)-4-(t-butyldimethylsilyloxy)-2,3-dihydroxy-4-phenylbutanoate

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Technology Process of ethyl (2R,3R,4S)-4-(t-butyldimethylsilyloxy)-2,3-dihydroxy-4-phenylbutanoate

There total 1 articles about ethyl (2R,3R,4S)-4-(t-butyldimethylsilyloxy)-2,3-dihydroxy-4-phenylbutanoate 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%

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

: 220384-85-0
ethyl (2R,3R,4S)-4-(t-butyldimethylsilyloxy)-2,3-dihydroxy-4-phenylbutanoate

Guidance literature:: With AD-mix-α; In water; tert-butyl alcohol; for 36h; Ambient temperature;
DOI:10.1016/S0040-4039(98)02269-2

Reference yield: 100.0%

: 1125-88-8
benzaldehyde dimethyl acetal

: 220384-85-0
ethyl (2R,3R,4S)-4-(t-butyldimethylsilyloxy)-2,3-dihydroxy-4-phenylbutanoate

: 220384-86-1
ethyl (2R,3R,4S)-2,3-benzylidenedioxy-4-(t-butyldimethylsilyloxy)-4-phenylbutanoate

Guidance literature:: With camphor-10-sulfonic acid; In benzene; for 1h; Heating;
DOI:10.1016/S0040-4039(98)02269-2

Reference yield:

: 220384-85-0
ethyl (2R,3R,4S)-4-(t-butyldimethylsilyloxy)-2,3-dihydroxy-4-phenylbutanoate

: 8-epi-9-deoxygoniopypyrone acetate

Guidance literature:: Multi-step reaction with 9 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

5.1: mesyl chloride; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5.2: 85 percent / NaH / methanol; diethyl ether / 1 h / 20 °C

6.1: n-BuLi; BF₃*Et₂O / tetrahydrofuran; hexane / 1 h / -78 °C

7.1: CF₃COOH / H₂O / 3 h / 20 °C

7.2: 82 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

8.1: 94 percent / TiCl₄ / CH₂Cl₂ / 0.5 h / 20 °C

9.1: 98 percent / DMAP / CH₂Cl₂ / 0.25 h / 20 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; dimethylsulfide borane complex; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; titanium tetrachloride; methanesulfonyl chloride; triethylamine; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; benzene; 1.1: Cyclization / 2.1: Reduction / 3.1: Ring cleavage / 3.2: Ring cleavage / 4.1: Acylation / 5.1: Substitution / 5.2: Epoxidation / 6.1: Julia coupling / 7.1: Cyclization / 7.2: Elimination / 8.1: debenzylation / 9.1: Acetylation;
DOI:10.1016/S0040-4020(99)00794-2