(4R,5S)-4-benzoyloxymethyl-6-(4-bromobenzyloxy)-5-tert-butyldimethyl-silyloxy-1-hexanal

Base Information

Chemical Name:(4R,5S)-4-benzoyloxymethyl-6-(4-bromobenzyloxy)-5-tert-butyldimethyl-silyloxy-1-hexanal
CAS No.:152732-87-1
Molecular Formula:C₂₇H₃₇BrO₅Si
Molecular Weight:549.577
Hs Code.:

Synonyms:(4R,5S)-4-benzoyloxymethyl-6-(4-bromobenzyloxy)-5-tert-butyldimethyl-silyloxy-1-hexanal

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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 (4R,5S)-4-benzoyloxymethyl-6-(4-bromobenzyloxy)-5-tert-butyldimethyl-silyloxy-1-hexanal

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Technology Process of (4R,5S)-4-benzoyloxymethyl-6-(4-bromobenzyloxy)-5-tert-butyldimethyl-silyloxy-1-hexanal

There total 5 articles about (4R,5S)-4-benzoyloxymethyl-6-(4-bromobenzyloxy)-5-tert-butyldimethyl-silyloxy-1-hexanal 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: 85.0%

: 152732-86-0
(2S,3R)-4-O-benzoyl-1-O-(4-bromobenzyl)-2-O-tert-butyldimethylsilyl-3-(3-hydroxypropyl)-1,2,4-butanetriol

: 152732-87-1
(4R,5S)-4-benzoyloxymethyl-6-(4-bromobenzyloxy)-5-tert-butyldimethyl-silyloxy-1-hexanal

Guidance literature:: With dipyridinium dichromate; acetic anhydride; In dichloromethane; N,N-dimethyl-formamide; at 40 ℃; for 1h;
DOI:10.1016/S0040-4020(01)96269-6

Reference yield:

: 132235-65-5
(2S,3R)-1-O-(p-bromobenzyl)-3-(2'-propenyl)-1,2,4-butanetriol

: 152732-87-1
(4R,5S)-4-benzoyloxymethyl-6-(4-bromobenzyloxy)-5-tert-butyldimethyl-silyloxy-1-hexanal

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

2: 99 percent / imidazole / dimethylformamide / 10 h / Ambient temperature

3: 1.) borane*dimethyl sulfide; 2.) sodium perborate / 1.) THF, 0 deg C, 10 min then r.t., 3 h; 2.) THF, H₂O, r.t., overnight

4: 85 percent / pyridinium dichromate, Ac₂O / CH₂Cl₂; dimethylformamide / 1 h / 40 °C

With pyridine; 1H-imidazole; dipyridinium dichromate; sodium perborate; dimethylsulfide borane complex; acetic anhydride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)96269-6

Reference yield:

: 132235-67-7
(2S,3R)-4-O-benzoyl-1-O-(p-bromobenzyl)-3-(2'-propenyl)-1,2,4-butanetriol

: 152732-87-1
(4R,5S)-4-benzoyloxymethyl-6-(4-bromobenzyloxy)-5-tert-butyldimethyl-silyloxy-1-hexanal

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / imidazole / dimethylformamide / 10 h / Ambient temperature

2: 1.) borane*dimethyl sulfide; 2.) sodium perborate / 1.) THF, 0 deg C, 10 min then r.t., 3 h; 2.) THF, H₂O, r.t., overnight

3: 85 percent / pyridinium dichromate, Ac₂O / CH₂Cl₂; dimethylformamide / 1 h / 40 °C

With 1H-imidazole; dipyridinium dichromate; sodium perborate; dimethylsulfide borane complex; acetic anhydride; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)96269-6