(1R,3R,4S,5R)-1,4-bis(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-6-oxabicyclo[3.2.1]octan-7-one

Base Information

Chemical Name:(1R,3R,4S,5R)-1,4-bis(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-6-oxabicyclo[3.2.1]octan-7-one
CAS No.:1352319-05-1
Molecular Formula:C₂₇H₃₆O₅Si
Molecular Weight:468.665
Hs Code.:

Synonyms:(1R,3R,4S,5R)-1,4-bis(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-6-oxabicyclo[3.2.1]octan-7-one

Suppliers and Price of (1R,3R,4S,5R)-1,4-bis(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-6-oxabicyclo[3.2.1]octan-7-one

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1R,3R,4S,5R)-1,4-bis(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-6-oxabicyclo[3.2.1]octan-7-one

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (1R,3R,4S,5R)-1,4-bis(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-6-oxabicyclo[3.2.1]octan-7-one

There total 2 articles about (1R,3R,4S,5R)-1,4-bis(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-6-oxabicyclo[3.2.1]octan-7-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: 60.0%

: 100-39-0
benzyl bromide

: 163217-18-3
(1R,3R,4S,5R)-3-[(tert-butyldimethylsilyl)oxy]-1,4-dihydroxy-6-oxa-bicyclo[3.2.1]octan-7-one

: 1352319-05-1
(1R,3R,4S,5R)-1,4-bis(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-6-oxabicyclo[3.2.1]octan-7-one

Guidance literature:: (1R,3R,4S,5R)-3-[(tert-butyldimethylsilyl)oxy]-1,4-dihydroxy-6-oxa-bicyclo[3.2.1]octan-7-one; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at 0 ℃; for 0.5h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; mineral oil; at 0 - 60 ℃; for 13.5h; Inert atmosphere;
DOI:10.1016/j.tetlet.2011.10.127

Reference yield:

: 77-95-2
D-(-)-quinic acid

: 1352319-05-1
(1R,3R,4S,5R)-1,4-bis(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-6-oxabicyclo[3.2.1]octan-7-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide; toluene / 12 h / Reflux

2.1: 1H-imidazole / N,N-dimethyl-formamide / 1.5 h / 0 - 20 °C / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere

3.2: 13.5 h / 0 - 60 °C / Inert atmosphere

With 1H-imidazole; sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; toluene; mineral oil;
DOI:10.1016/j.tetlet.2011.10.127

Reference yield:

: 1352319-05-1
(1R,3R,4S,5R)-1,4-bis(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-6-oxabicyclo[3.2.1]octan-7-one

: 2450-53-5,16758-05-7,89919-61-9,89919-62-0,101222-97-3
3,5-di-O-caffeoylquinic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: water; sodium hydroxide / tetrahydrofuran / 0.75 h / 20 °C

2.1: caesium carbonate / methanol / pH 7

2.2: 11 h / 0 - 20 °C / Inert atmosphere

3.1: pyridine hydrofluoride / tetrahydrofuran / 12 h / 0 - 20 °C

4.1: toluene / 5 h / 60 °C / Inert atmosphere

5.1: 10% Pd(OH)₂ on C; hydrogen / methanol / 36 h / 20 °C

6.1: piperidine; dmap / N,N-dimethyl-formamide / 192 h / 20 °C / Inert atmosphere

With piperidine; dmap; pyridine hydrofluoride; 10% Pd(OH)₂ on C; water; hydrogen; caesium carbonate; sodium hydroxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; 6.1: Knoevenagel condensation;
DOI:10.1016/j.tetlet.2011.10.127