(2R,3S,4R)-4-benzoyloxy-3-[4-(tert-butyldimethylsilyloxy)butoxy]hex-5-ene-1,2-diol

Base Information

• Chemical Name: (2R,3S,4R)-4-benzoyloxy-3-[4-(tert-butyldimethylsilyloxy)butoxy]hex-5-ene-1,2-diol
• CAS No.: 794516-10-2
• Molecular Formula: C₂₃H₃₈O₆Si
• Molecular Weight: 438.637

Synonyms:(2R,3S,4R)-4-benzoyloxy-3-[4-(tert-butyldimethylsilyloxy)butoxy]hex-5-ene-1,2-diol

Chemical Property of (2R,3S,4R)-4-benzoyloxy-3-[4-(tert-butyldimethylsilyloxy)butoxy]hex-5-ene-1,2-diol

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3S,4R)-4-benzoyloxy-3-[4-(tert-butyldimethylsilyloxy)butoxy]hex-5-ene-1,2-diol

There total 5 articles about (2R,3S,4R)-4-benzoyloxy-3-[4-(tert-butyldimethylsilyloxy)butoxy]hex-5-ene-1,2-diol 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: 81.0%

methyl 4-O-benzoyl-6-bromo-3-O-[4-{(tert-butyldimethylsilyl)oxy}butyl]-6-deoxy-α-D-altropyranoside (299410-98-3) → (2R,3S,4R)-4-benzoyloxy-3-[4-(tert-butyldimethylsilyloxy)butoxy]hex-5-ene-1,2-diol (794516-10-2)

Guidance literature:

With sodium cyanoborohydride; zinc; In propan-1-ol; water; at 95 ℃;

DOI:10.1021/jo0491051

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (2R,3S,4R)-4-benzoyloxy-3-[4-(tert-butyldimethylsilyloxy)butoxy]hex-5-ene-1,2-diol (794516-10-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 3.9 g / Et₃N; DMAP / CH₂Cl₂ / 19 h / 20 °C

2: 75 percent / BaCO₃; NBS / CCl₄ / Heating

3: 81 percent / Zn; NaBH₃CN / propan-1-ol; H₂O / 95 °C

With dmap; N-Bromosuccinimide; sodium cyanoborohydride; triethylamine; barium carbonate; zinc; In propan-1-ol; tetrachloromethane; dichloromethane; water;

DOI:10.1021/jo0491051

Reference yield:

(2R,4aR,6S,7S,8S,8aR)-8-(4-Hydroxy-butoxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (299410-94-9) → (2R,3S,4R)-4-benzoyloxy-3-[4-(tert-butyldimethylsilyloxy)butoxy]hex-5-ene-1,2-diol (794516-10-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 3.9 g / Et₃N; DMAP / CH₂Cl₂ / 19 h / 20 °C

2: 75 percent / BaCO₃; NBS / CCl₄ / Heating

3: 81 percent / Zn; NaBH₃CN / propan-1-ol; H₂O / 95 °C

With dmap; N-Bromosuccinimide; sodium cyanoborohydride; triethylamine; barium carbonate; zinc; In propan-1-ol; tetrachloromethane; dichloromethane; water;

DOI:10.1021/jo0491051

upstream raw materials:

methyl 4-O-benzoyl-6-bromo-3-O-[4-{(tert-butyldimethylsilyl)oxy}butyl]-6-deoxy-α-D-altropyranoside

tert-butyldimethylsilyl chloride

(2R,4aR,6S,7S,8S,8aR)-8-(4-Hydroxy-butoxy)-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

methyl 4,6-O-benzylidene-3-O-[4-{(tert-butyldimethylsilyl)oxy}butyl]-α-D-altropyranoside

Downstream raw materials:

(3R,4R,5R)-3-benzoyloxy-4-[4-(tert-butyldimethylsilyloxy)butoxy]-5,6-epoxyhex-1-ene

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