(2S,3R)-3-Azido-4-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-butan-2-ol

Base Information

Chemical Name:(2S,3R)-3-Azido-4-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-butan-2-ol
CAS No.:177957-91-4
Molecular Formula:C₂₈H₃₅N₃O₄Si
Molecular Weight:505.689
Hs Code.:

Synonyms:(2S,3R)-3-Azido-4-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-butan-2-ol

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Chemical Property of (2S,3R)-3-Azido-4-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-butan-2-ol

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Technology Process of (2S,3R)-3-Azido-4-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-butan-2-ol

There total 8 articles about (2S,3R)-3-Azido-4-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-butan-2-ol 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: 91.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 177957-88-9
[S-(R,S)]-2-azido-4-[(4-methoxyphenyl)methoxy]-1,3-butanediol

: 177957-91-4
(2S,3R)-3-Azido-4-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-butan-2-ol

Guidance literature:: With dmap; triethylamine; In dichloromethane; Ambient temperature;
DOI:10.1016/0040-4039(96)00594-1

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 177957-91-4
(2S,3R)-3-Azido-4-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-butan-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 74 percent / NaH / paraffin; dimethylformamide / 3 h / Ambient temperature

2: L-(+)-DET, Ti(O-i-Pr)4, TBHP, molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 70 h / -20 °C

3: 55 percent / NaN₃, NH₄Cl / ethanol / 17 h / Heating

4: 91 percent / Et₃N, DMAP / CH₂Cl₂ / 17 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium azide; molecular sieve; diethyl (2R,3R)-tartrate; sodium hydride; ammonium chloride; triethylamine; In 2,2,4-trimethylpentane; ethanol; dichloromethane; N,N-dimethyl-formamide; paraffin;
DOI:10.1016/S0040-4020(97)00651-0

Reference yield:

: 177957-84-5
(2S,3S)-3-(O-benzyl)-4-[O-(p-methoxy)benzyl]-1,2,3,4-butanetetraol-1,2-di-O-acetonide

: 177957-91-4
(2S,3R)-3-Azido-4-(tert-butyl-diphenyl-silanyloxy)-1-(4-methoxy-benzyloxy)-butan-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / H₂ / Raney Ni / ethanol / 1 h / 760 Torr / Ambient temperature

2: 100 percent / Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: 97 percent / aq. HCl / methanol / 0.5 h / Ambient temperature

4: 88 percent / K₂CO₃ / methanol / 0.5 h / Ambient temperature

5: 55 percent / NaN₃, NH₄Cl / ethanol / 17 h / Heating

6: 91 percent / Et₃N, DMAP / CH₂Cl₂ / 17 h / Ambient temperature

With hydrogenchloride; dmap; sodium azide; hydrogen; potassium carbonate; ammonium chloride; triethylamine; nickel; In methanol; ethanol; dichloromethane;
DOI:10.1016/S0040-4020(97)00651-0