Benzoic acid (4S,5R)-5-[(1S,2S)-1-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Base Information

Chemical Name:Benzoic acid (4S,5R)-5-[(1S,2S)-1-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester
CAS No.:176723-02-7
Molecular Formula:C₂₇H₄₃NO₈Si
Molecular Weight:537.726
Hs Code.:

Benzoic acid (4S,5R)-5-[(1S,2S)-1-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

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Chemical Property of Benzoic acid (4S,5R)-5-[(1S,2S)-1-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

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Technology Process of Benzoic acid (4S,5R)-5-[(1S,2S)-1-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

There total 9 articles about Benzoic acid (4S,5R)-5-[(1S,2S)-1-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl 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:

: Benzoic acid (4S,5R)-5-[(1S,2S,3R)-1-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3,4-dihydroxy-butyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

: 176723-02-7
Benzoic acid (4S,5R)-5-[(1S,2S)-1-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Guidance literature:: With sodium periodate; silica gel; In dichloromethane; for 3h; Yield given;
DOI:10.1016/0040-4020(96)00151-2

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 176723-02-7
Benzoic acid (4S,5R)-5-[(1S,2S)-1-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: imidazole / dimethylformamide / 12 h

2: 1.) KMnO₄, cis-dicyclohexano-18-crown-6 ether, 2.) TsOH / 1.) CH₂Cl₂, 2 h, 2.) 1 h

3: 1M aq. LiOH / 3 h

4: diethyl ether

5: NaBH₄, (C₁₈H₁₇)3N(+)CH₃Cl(-) / benzene; H₂O / 12 h / Heating

6: DMAP / pyridine / 2 h / Ambient temperature

7: 70percent aq. AcOH / 12 h / 50 - 60 °C

8: SiO₂, aq. NaIO₄ / CH₂Cl₂ / 3 h

With 1H-imidazole; dmap; lithium hydroxide; sodium tetrahydroborate; potassium permanganate; sodium periodate; (C₁₈H₁₇)3N(+)CH₃Cl(-); dicyclohexano-18-crown-6; silica gel; toluene-4-sulfonic acid; acetic acid; In pyridine; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/0040-4020(96)00151-2

Reference yield:

: 141393-83-1
(4S,5S,6R)-N-(tert-butoxycarbonyl)-6,7-O-isopropylidene-2,3-dideoxy-hept-2-enono-1,4-lactam

: 176723-02-7
Benzoic acid (4S,5R)-5-[(1S,2S)-1-tert-butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-oxo-propyl]-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: imidazole / dimethylformamide / 12 h

2: 1.) KMnO₄, cis-dicyclohexano-18-crown-6 ether, 2.) TsOH / 1.) CH₂Cl₂, 2 h, 2.) 1 h

3: 1M aq. LiOH / 3 h

4: diethyl ether

5: NaBH₄, (C₁₈H₁₇)3N(+)CH₃Cl(-) / benzene; H₂O / 12 h / Heating

6: DMAP / pyridine / 2 h / Ambient temperature

7: 70percent aq. AcOH / 12 h / 50 - 60 °C

8: SiO₂, aq. NaIO₄ / CH₂Cl₂ / 3 h

With 1H-imidazole; dmap; lithium hydroxide; sodium tetrahydroborate; potassium permanganate; sodium periodate; (C₁₈H₁₇)3N(+)CH₃Cl(-); dicyclohexano-18-crown-6; silica gel; toluene-4-sulfonic acid; acetic acid; In pyridine; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; benzene;
DOI:10.1016/0040-4020(96)00151-2