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

Base Information

• Chemical Name: (1S,4S,5R,6R)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enol
• CAS No.: 139209-35-1
• Molecular Formula: C₂₅H₄₄O₄Si₂
• Molecular Weight: 464.793

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

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

Chemical Property:

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

There total 11 articles about (1S,4S,5R,6R)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enol 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: 98.0%

(4S,5R,6S)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enone (139209-34-0) → (1S,4S,5R,6R)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enol (139209-35-1)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; for 12h; -78 deg C to r.t.;

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

Reference yield:

(4S,5R,6S)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enone (139209-34-0) → (1R,4S,5R,6R)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enol (139209-35-1) + (1S,4S,5R,6R)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enol (139209-35-1)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃; Yield given. Yields of byproduct given;

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

Reference yield:

(4S,5R,6S)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enone (139209-34-0) → (1R,4S,5R,6R)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enol (139209-35-1) + (1S,4S,5R,6R)-5-Benzyloxy-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enol (139209-35-1)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 ℃; Yield given. Yields of byproduct given;

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

upstream raw materials:

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

t-butyldimethylsiyl triflate

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

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

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