(1S,2S,3R,4S,5S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-3-triethylsilanyloxy-cyclohexanol

Base Information

Chemical Name:(1S,2S,3R,4S,5S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-3-triethylsilanyloxy-cyclohexanol
CAS No.:462099-69-0
Molecular Formula:C₂₅H₅₆O₅Si₃
Molecular Weight:520.973
Hs Code.:

Synonyms:(1S,2S,3R,4S,5S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-3-triethylsilanyloxy-cyclohexanol

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Chemical Property of (1S,2S,3R,4S,5S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-3-triethylsilanyloxy-cyclohexanol

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Technology Process of (1S,2S,3R,4S,5S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-3-triethylsilanyloxy-cyclohexanol

There total 5 articles about (1S,2S,3R,4S,5S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-3-triethylsilanyloxy-cyclohexanol 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: 59.0%

: (1R,2S,3R,4S,5S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-3-triethylsilanyloxy-6-oxa-bicyclo[3.2.1]octan-7-one

: 462099-69-0
(1S,2S,3R,4S,5S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-3-triethylsilanyloxy-cyclohexanol

Guidance literature:: With lithium borohydride; In tetrahydrofuran;
DOI:10.1002/1099-0690(200206)2002:12<1956::AID-EJOC1956>3.0.CO;2-Y

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 462099-69-0
(1S,2S,3R,4S,5S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-3-triethylsilanyloxy-cyclohexanol

Guidance literature:: Multi-step reaction with 2 steps

1: 74 percent / DIPEA / CH₂Cl₂

2: 59 percent / LiBH₄ / tetrahydrofuran

With lithium borohydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1: Mukaiyama-type cycloaldolization;
DOI:10.1002/1099-0690(200206)2002:12<1956::AID-EJOC1956>3.0.CO;2-Y

Reference yield:

: 384341-88-2
(S)-5-[(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxy)-2,3-dihydroxy-propyl]-dihydro-furan-2-one

: 462099-69-0
(1S,2S,3R,4S,5S)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-3-triethylsilanyloxy-cyclohexanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 98 percent / DMAP / pyridine

2.1: oxalyl chloride; DMSO / CH₂Cl₂ / 0.83 h / -40 - -15 °C

2.2: 70 percent / Et₃N / CH₂Cl₂ / 1.08 h / -40 - 25 °C

3.1: 74 percent / DIPEA / CH₂Cl₂

4.1: 59 percent / LiBH₄ / tetrahydrofuran

With dmap; lithium borohydride; oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; dichloromethane; 2.1: modified Swern oxidation / 3.1: Mukaiyama-type cycloaldolization;
DOI:10.1002/1099-0690(200206)2002:12<1956::AID-EJOC1956>3.0.CO;2-Y