(1S,2S,3S,5S)-5-benzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane

Base Information

• Chemical Name: (1S,2S,3S,5S)-5-benzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane
• CAS No.: 144118-53-6
• Molecular Formula: C₁₇H₂₂O₅
• Molecular Weight: 306.359
• Mol file: 144118-53-6.mol

Synonyms:(1S,2S,3S,5S)-5-benzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane

Chemical Property of (1S,2S,3S,5S)-5-benzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (1S,2S,3S,5S)-5-benzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane

There total 2 articles about (1S,2S,3S,5S)-5-benzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane 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: 95.0%

methyl 3-O-benzyl-6-bromo-2-carbomethoxymethylidene-4,6-dideoxy-α-D-treohexopyranoside → (1S,2S,3S,5S)-5-benzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane (144118-53-6) + ((1R,3R,4R,5S)-5-Benzyloxy-3-methoxy-2-oxa-bicyclo[2.2.1]hept-4-yl)-acetic acid methyl ester

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 3h; Heating;

DOI:10.1007/BF00699015

Reference yield: 40.4%

methanol (67-56-1) + (1S,2S,4S,6S)-2-methoxy-6-benzylhydroxy-1-ethoxycarbonylmethylene-3-oxabicyclo<2.2.1>heptane (144118-52-5) → (1S,2S,3S,5S)-5-benzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane (144118-53-6)

Guidance literature:

With sulfuric acid; 1.) 25 deg C, 24 h, 2.) reflux, 1 h;

DOI:10.1007/BF00863074

Reference yield: 93.0%

(1S,2S,3S,5S)-5-benzyloxy-3-methoxy-4-methoxycarbonylmethyl-2-oxabicyclo<2.2.1>heptane (144118-53-6) → (1S,3S,4S,5S)-5-benzyloxy-4-(β-hydroxyethyl)-3-methoxy-2-oxabicyclo<2.2.1>heptane

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1h; Heating;

DOI:10.1007/BF00699015

upstream raw materials:

methanol

(1S,2S,4S,6S)-2-methoxy-6-benzylhydroxy-1-ethoxycarbonylmethylene-3-oxabicyclo<2.2.1>heptane