(1S,3R,4R,5S,2'R)-4-benzyloxy-3-benzyloxymethyl-2,8-dioxabicyclo<3.3.0>octane-6-spiro-2'-oxirane

Base Information

• Chemical Name: (1S,3R,4R,5S,2'R)-4-benzyloxy-3-benzyloxymethyl-2,8-dioxabicyclo<3.3.0>octane-6-spiro-2'-oxirane
• CAS No.: 141357-10-0
• Molecular Formula: C₂₂H₂₄O₅
• Molecular Weight: 368.43

Synonyms:(1S,3R,4R,5S,2'R)-4-benzyloxy-3-benzyloxymethyl-2,8-dioxabicyclo<3.3.0>octane-6-spiro-2'-oxirane

Chemical Property of (1S,3R,4R,5S,2'R)-4-benzyloxy-3-benzyloxymethyl-2,8-dioxabicyclo<3.3.0>octane-6-spiro-2'-oxirane

Chemical Property:

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Technology Process of (1S,3R,4R,5S,2'R)-4-benzyloxy-3-benzyloxymethyl-2,8-dioxabicyclo<3.3.0>octane-6-spiro-2'-oxirane

There total 3 articles about (1S,3R,4R,5S,2'R)-4-benzyloxy-3-benzyloxymethyl-2,8-dioxabicyclo<3.3.0>octane-6-spiro-2'-oxirane 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: 74.0%

(1S,3R,4R,5R)-4-benzyloxy-3-benzyloxymethyl-6-methylene-2,8-dioxabicyclo<3.3.0>octane (141357-06-4) → (1S,3R,4R,5S,2'R)-4-benzyloxy-3-benzyloxymethyl-2,8-dioxabicyclo<3.3.0>octane-6-spiro-2'-oxirane (141357-10-0)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/0008-6215(92)84064-Y

Reference yield:

propargyl 3,5-di-O-benzyl-α-D-xylofuranoside (141379-61-5) → (1S,3R,4R,5S,2'R)-4-benzyloxy-3-benzyloxymethyl-2,8-dioxabicyclo<3.3.0>octane-6-spiro-2'-oxirane (141357-10-0)

Guidance literature:

Multi-step reaction with 3 steps

2: 87 percent / Bu3SnH, α,α'-azobisisobutyronitrile / benzene / 1 h / Heating

3: 74 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 2 h / Ambient temperature

With azobisisobutyronitrile; tri-n-butyl-tin hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; benzene;

DOI:10.1016/0008-6215(92)84064-Y

Reference yield:

propargyl 3,5-di-O-benzyl-2-O<(S-methylthio)thiocarbonyl>-α-D-xylofuranoside (141357-08-6) → (1S,3R,4R,5S,2'R)-4-benzyloxy-3-benzyloxymethyl-2,8-dioxabicyclo<3.3.0>octane-6-spiro-2'-oxirane (141357-10-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / Bu3SnH, α,α'-azobisisobutyronitrile / benzene / 1 h / Heating

2: 74 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 2 h / Ambient temperature

With azobisisobutyronitrile; tri-n-butyl-tin hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; benzene;

DOI:10.1016/0008-6215(92)84064-Y

upstream raw materials:

(1S,3R,4R,5R)-4-benzyloxy-3-benzyloxymethyl-6-methylene-2,8-dioxabicyclo<3.3.0>octane

propargyl 3,5-di-O-benzyl-α-D-xylofuranoside

propargyl 3,5-di-O-benzyl-2-O<(S-methylthio)thiocarbonyl>-α-D-xylofuranoside

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