(3S,4R,5S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hexanal

Base Information

Chemical Name:(3S,4R,5S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hexanal
CAS No.:155299-98-2
Molecular Formula:C₂₁H₃₆O₃Si
Molecular Weight:364.601
Hs Code.:

Synonyms:(3S,4R,5S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hexanal

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Chemical Property of (3S,4R,5S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hexanal

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Technology Process of (3S,4R,5S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hexanal

There total 7 articles about (3S,4R,5S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-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%

: 155299-97-1
(3S,4R,5S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hexan-1-ol

: 155299-98-2
(3S,4R,5S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hexanal

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1016/0040-4020(95)00201-I

Reference yield:

: 106357-30-6
1-benzyloxy-2(S),4(S)-dimethyl-hex-5-en-3(R)-ol

: 155299-98-2
(3S,4R,5S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hexanal

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / -30 °C

2: 1.) 9-BBN, 2.) H₂O₂, NaOH / 1.) THF, reflux, 2 h, 2.) THF, H₂O, r.t., 1 h

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 15 min

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1039/a804170i

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 155299-98-2
(3S,4R,5S)-6-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-hexanal

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / Et₃N / CH₂Cl₂ / -30 °C

2: 1.) 9-BBN, 2.) NaOH, H₂O₂ / 1.) THF, 2.) THF, heating

3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 2.) CH₂Cl₂, r.t.

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; dihydrogen peroxide; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1016/S0040-4039(00)76542-7