(1S,4S,5S,6S)-6-Benzyloxy-2,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[2.2.1]hept-2-ene

Base Information

• Chemical Name: (1S,4S,5S,6S)-6-Benzyloxy-2,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[2.2.1]hept-2-ene
• CAS No.: 144677-77-0
• Molecular Formula: C₂₅H₄₂O₄Si₂
• Molecular Weight: 462.777

Synonyms:(1S,4S,5S,6S)-6-Benzyloxy-2,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[2.2.1]hept-2-ene

Chemical Property of (1S,4S,5S,6S)-6-Benzyloxy-2,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[2.2.1]hept-2-ene

Chemical Property:

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Technology Process of (1S,4S,5S,6S)-6-Benzyloxy-2,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[2.2.1]hept-2-ene

There total 3 articles about (1S,4S,5S,6S)-6-Benzyloxy-2,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[2.2.1]hept-2-ene 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:

(+/-)-(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) → (1S,4S,5S,6S)-6-Benzyloxy-2,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[2.2.1]hept-2-ene (144677-77-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / imidazole / dimethylformamide

2: 1) (Me₃Si)2NK / THF, -78 deg C

With 1H-imidazole; potassium hexamethylsilazane; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)79144-1

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (1S,4S,5S,6S)-6-Benzyloxy-2,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[2.2.1]hept-2-ene (144677-77-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / imidazole / dimethylformamide

2: 1) (Me₃Si)2NK / THF, -78 deg C

With 1H-imidazole; potassium hexamethylsilazane; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)79144-1

Reference yield:

(1RS,4RS,5RS,6SR)-6-endo-(benzyloxy)-5-exo-{[(t-butyl)dimethylsilyl]oxy}-7-oxabicyclo[2.2.1]heptan-2-one (139391-31-4,139491-27-3) + tert-butyldimethylsilyl chloride (18162-48-6) → (1S,4S,5S,6S)-6-Benzyloxy-2,5-bis-(tert-butyl-dimethyl-silanyloxy)-7-oxa-bicyclo[2.2.1]hept-2-ene (144677-77-0)

Guidance literature:

With potassium hexamethylsilazane; Yield given. Multistep reaction; THF, -78 deg C;

DOI:10.1016/S0040-4039(00)79144-1

upstream raw materials:

(1RS,4RS,5RS,6SR)-6-endo-(benzyloxy)-5-exo-{[(t-butyl)dimethylsilyl]oxy}-7-oxabicyclo[2.2.1]heptan-2-one

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

(1R,2S,3S,4S,5S,6S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxymethyl-7-oxa-bicyclo[2.2.1]heptan-2-ol

(1S,3R,4S,5S,6S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxymethyl-7-oxa-bicyclo[2.2.1]heptan-2-one

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