(+/-)-(1R,2R,3S,4R,6S)-4,6-diazido-2-[(tert-butyldimethylsilyl)oxy]cyclohexane-1,3-diol

Base Information

Chemical Name:(+/-)-(1R,2R,3S,4R,6S)-4,6-diazido-2-[(tert-butyldimethylsilyl)oxy]cyclohexane-1,3-diol
CAS No.:727719-91-7
Molecular Formula:C₁₂H₂₄N₆O₃Si
Molecular Weight:328.446
Hs Code.:

Synonyms:(+/-)-(1R,2R,3S,4R,6S)-4,6-diazido-2-[(tert-butyldimethylsilyl)oxy]cyclohexane-1,3-diol

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Chemical Property of (+/-)-(1R,2R,3S,4R,6S)-4,6-diazido-2-[(tert-butyldimethylsilyl)oxy]cyclohexane-1,3-diol

Chemical Property:

Purity/Quality:

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Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (+/-)-(1R,2R,3S,4R,6S)-4,6-diazido-2-[(tert-butyldimethylsilyl)oxy]cyclohexane-1,3-diol

There total 7 articles about (+/-)-(1R,2R,3S,4R,6S)-4,6-diazido-2-[(tert-butyldimethylsilyl)oxy]cyclohexane-1,3-diol 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: 82.0%

: (+/-)-(1S,2R,3R,4R,6R)-6-azido-2-[(tert-butyldimethylsilyl)oxy]-3,4-epoxycyclohexan-1-ol

: 727719-91-7
(+/-)-(1R,2R,3S,4R,6S)-4,6-diazido-2-[(tert-butyldimethylsilyl)oxy]cyclohexane-1,3-diol

Guidance literature:: With sodium azide; triethylamine; ytterbium(III) triflate; 4 A molecular sieve; In toluene; at 80 ℃; for 96h;
DOI:10.1021/jo049788k

Reference yield: 81.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 90899-14-2
(1α,2β,3α,4β,6β)-4,6-Diazido-1,2,3-cyclohexantriol

: 727719-91-7
(+/-)-(1R,2R,3S,4R,6S)-4,6-diazido-2-[(tert-butyldimethylsilyl)oxy]cyclohexane-1,3-diol

Guidance literature:: With 2,6-dimethylpyridine; In tetrahydrofuran; at 0 - 20 ℃; for 3h; Inert atmosphere;
DOI:10.1039/c7cc05052f

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 727719-91-7
(+/-)-(1R,2R,3S,4R,6S)-4,6-diazido-2-[(tert-butyldimethylsilyl)oxy]cyclohexane-1,3-diol

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / DIPEA; DMAP / CH₂Cl₂ / 5 h / 20 °C

2: 85 percent / NaN₃; NH₄Cl / methanol / 40 h / Heating

3: 72 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 20 °C

4: 82 percent / Yb(OTf)3; Et₃N; NaN₃ / molecular sieves 4 Angstroem / toluene / 96 h / 80 °C

With dmap; sodium azide; ammonium chloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; ytterbium(III) triflate; 4 A molecular sieve; In methanol; dichloromethane; toluene;
DOI:10.1021/jo049788k