(-)-(1R,4R,5R,6S)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one

Base Information

• Chemical Name: (-)-(1R,4R,5R,6S)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one
• CAS No.: 129829-54-5
• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.252

Synonyms:(-)-(1R,4R,5R,6S)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one

Chemical Property of (-)-(1R,4R,5R,6S)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one

Chemical Property:

Purity/Quality:

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Technology Process of (-)-(1R,4R,5R,6S)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one

There total 10 articles about (-)-(1R,4R,5R,6S)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one 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: 88.0%

(1RS,4RS,5RS,6RS)-2,2-bis(benzyloxy)-5,6-exo-epoxy-2,2-7-oxabicyclo<2.2.1>heptane + benzyl alcohol (100-51-6,185532-71-2) → (+/-)-(1R,4R,5R,6S)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one (115140-20-0,129829-54-5,139342-54-4)

Guidance literature:

With fluorosulphonic acid; In dichloromethane; at 20 ℃;

DOI:10.1002/hlca.19870700706

Reference yield: 88.0%

(1R,5R)-6,6-Bis-benzyloxy-3,8-dioxa-tricyclo[3.2.1.02,4]octane (115140-10-8,129829-53-4) → (1R,4R,5R,6S)-6-Benzyloxy-5-hydroxy-7-oxa-bicyclo[2.2.1]heptan-2-one (115140-20-0,129829-54-5,139342-54-4)

Guidance literature:

With fluorosulphonic acid; benzyl alcohol; In dichloromethane;

DOI:10.1016/S0040-4039(00)82156-5

Reference yield: 87.0%

(+)-(1R,4R,5R,6R)-2,2-bis(benzyloxy)-5,6-exo-epoxy-7-oxabicyclo<2.2.1>heptane (129829-53-4) + benzyl alcohol (100-51-6,185532-71-2) → (-)-(1R,4R,5R,6S)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one (129829-54-5)

Guidance literature:

With fluorosulphonic acid; In dichloromethane;

DOI:10.1002/hlca.19900730118

upstream raw materials:

benzyl alcohol

(+/-)-7-oxabicyclo<2.2.1>hept-5-en-2-one

7-oxabicyclo<2.2.1>hept-5-en-2-one dibenzyl acetal

(1RS,2RS)-5,5-bis(benzyloxy)-7-oxabicyclo<2.2.1>hept-2-ene

Downstream raw materials:

(-)-(1R,4R,5R,6S)-6-endo-(benzyloxy)-5-exo-(methoxymethoxy)-7-oxabicyclo[2.2.1]heptan-2-one

(-)-(1R,2S,3S,4R)-1,2,3,4-tetraacetoxy-5-cyclohexene

(-)-(4R,5S,6R)-4,5,6-tris(<(tert-butyl)dimethylsilyl>oxy)cyclohex-2-en-1-one

(-)-1D-2,3,4-tris-O-<(tert-butyl)dimethylsilyl>cyclohex-2-ene-1,2,4/3-tetrol

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