(2R,3S,4R,5S)-4-Azido-1,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-hexane-2,3-diol

Base Information

Chemical Name:(2R,3S,4R,5S)-4-Azido-1,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-hexane-2,3-diol
CAS No.:881894-94-6
Molecular Formula:C₃₆H₄₃N₃O₅Si
Molecular Weight:625.84
Hs Code.:

Synonyms:(2R,3S,4R,5S)-4-Azido-1,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-hexane-2,3-diol

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Chemical Property of (2R,3S,4R,5S)-4-Azido-1,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-hexane-2,3-diol

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Technology Process of (2R,3S,4R,5S)-4-Azido-1,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-hexane-2,3-diol

There total 6 articles about (2R,3S,4R,5S)-4-Azido-1,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-hexane-2,3-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: 100.0%

: 881895-23-4
(2S,3R,4S,5R)-3-Azido-2,6-bis-benzyloxy-hexane-1,4,5-triol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 881894-94-6
(2R,3S,4R,5S)-4-Azido-1,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-hexane-2,3-diol

Guidance literature:: With pyridine; at 20 ℃; for 3h;
DOI:10.1021/ol0601996

Reference yield:

: 872593-83-4
p-tolyl 2,3-anhydro-4,6-O-benzylidene-1-thio-β-D-mannopyranoside

: 881894-94-6
(2R,3S,4R,5S)-4-Azido-1,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-hexane-2,3-diol

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / sodium azide; ammonium chloride / dimethylsulfoxide / 6 h / 80 °C

2: 86 percent / sodium hydride / dimethylformamide / 30 h / 20 °C

3: 95 percent / sodium cyanoborohydride; HCl*Et₂O / tetrahydrofuran / 0.17 h / 20 °C

4: 92 percent / N-bromosuccinimide / acetone; H₂O / 20 °C

5: 86 percent / sodium borohydride / methanol; H₂O / 1 h / 20 °C

6: 100 percent / pyridine / 3 h / 20 °C

With pyridine; sodium tetrahydroborate; N-Bromosuccinimide; sodium azide; ammonium chloride; hydrochloric acid diethyl ether; sodium hydride; sodium cyanoborohydride; In tetrahydrofuran; methanol; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ol0601996

Reference yield:

: 881895-22-3
(3S,4R,5S,6R)-4-Azido-3-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2,5-diol

: 881894-94-6
(2R,3S,4R,5S)-4-Azido-1,5-bis-benzyloxy-6-(tert-butyl-diphenyl-silanyloxy)-hexane-2,3-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / sodium borohydride / methanol; H₂O / 1 h / 20 °C

2: 100 percent / pyridine / 3 h / 20 °C

With pyridine; sodium tetrahydroborate; In methanol; water;
DOI:10.1021/ol0601996