Acetic acid (1R,2R,3S)-3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-vinyl-butyl ester

Base Information

Chemical Name:Acetic acid (1R,2R,3S)-3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-vinyl-butyl ester
CAS No.:144001-83-2
Molecular Formula:C₂₂H₃₅NO₆Si
Molecular Weight:437.608
Hs Code.:

Synonyms:Acetic acid (1R,2R,3S)-3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-vinyl-butyl ester

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Chemical Property of Acetic acid (1R,2R,3S)-3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-vinyl-butyl ester

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Technology Process of Acetic acid (1R,2R,3S)-3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-vinyl-butyl ester

There total 9 articles about Acetic acid (1R,2R,3S)-3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-vinyl-butyl ester 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:

: 144001-93-4
Acetic acid (1R,2R,3R)-3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-oxo-1-vinyl-butyl ester

: 144001-83-2
Acetic acid (1R,2R,3S)-3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-vinyl-butyl ester

Guidance literature:: With sodium tetrahydroborate; In tetrahydrofuran; water; at -43 ℃; Yield given;
DOI:10.1021/jo00048a006

Reference yield:

: 1078691-95-8
(+)-D-glucosamine hydrochloride

: 144001-83-2
Acetic acid (1R,2R,3S)-3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-vinyl-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: NaHCO₃ / dioxane; H₂O / 24 °C

2: HCl / 24 h / Heating

3: CSA / dimethylformamide / 80 °C

4: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

5: 73 percent / (NH₄)2Ce(NO₃)6 / acetonitrile; H₂O / 1 h / 25 °C

6: 88 percent / iodine, Ph₃P, pyridine / toluene / 70 °C

7: 98 percent / pyridine, DMAP / CH₂Cl₂ / 24 °C

8: activated Zn, 95 percent EtOH / 1 h / 78 °C

9: NaBH₄ / tetrahydrofuran; H₂O / -43 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium tetrahydroborate; ammonium cerium(IV) nitrate; ethanol; camphor-10-sulfonic acid; iodine; sodium hydrogencarbonate; triphenylphosphine; zinc; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo00048a006

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 144001-83-2
Acetic acid (1R,2R,3S)-3-benzyloxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-1-vinyl-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: NaHCO₃ / dioxane; H₂O / 24 °C

2: HCl / 24 h / Heating

3: CSA / dimethylformamide / 80 °C

4: 90 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

5: 73 percent / (NH₄)2Ce(NO₃)6 / acetonitrile; H₂O / 1 h / 25 °C

6: 88 percent / iodine, Ph₃P, pyridine / toluene / 70 °C

7: 98 percent / pyridine, DMAP / CH₂Cl₂ / 24 °C

8: activated Zn, 95 percent EtOH / 1 h / 78 °C

9: NaBH₄ / tetrahydrofuran; H₂O / -43 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium tetrahydroborate; ammonium cerium(IV) nitrate; ethanol; camphor-10-sulfonic acid; iodine; sodium hydrogencarbonate; triphenylphosphine; zinc; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1021/jo00048a006