(4S,5R,6S)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enone

Base Information

• Chemical Name: (4S,5R,6S)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enone
• CAS No.: 139209-34-0
• Molecular Formula: C₂₅H₄₂O₄Si₂
• Molecular Weight: 462.777

Synonyms:(4S,5R,6S)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enone

Chemical Property of (4S,5R,6S)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enone

Chemical Property:

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Technology Process of (4S,5R,6S)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enone

There total 3 articles about (4S,5R,6S)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enone 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:

(-)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one (139342-54-4) → (4S,5R,6S)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enone (139209-34-0)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide

2: Et₃N / benzene

With 1H-imidazole; triethylamine; In N,N-dimethyl-formamide; benzene;

DOI:10.1016/0040-4039(91)80506-2

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (4S,5R,6S)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enone (139209-34-0)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide

2: Et₃N / benzene

With 1H-imidazole; triethylamine; In N,N-dimethyl-formamide; benzene;

DOI:10.1016/0040-4039(91)80506-2

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) + (1S,4S,5S,6R)-6-endo-(benzyloxy)-5-exo-<<(t-butyl)dimethylsilyl>oxy>-7-oxabicyclo<2.2.1>heptan-2-one (139391-31-4) → (4S,5R,6S)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enone (139209-34-0)

Guidance literature:

With triethylamine; In benzene; Yield given;

DOI:10.1016/0040-4039(91)80506-2

upstream raw materials:

t-butyldimethylsiyl triflate

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

(-)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one

tert-butyldimethylsilyl chloride

Downstream raw materials:

(1R,4S,5R,6R)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enol

(1S,4S,5R,6R)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enol

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