(Z)-(4S,5R)-5-Acetylamino-4-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-pent-2-enoic acid methyl ester

Base Information

Chemical Name:(Z)-(4S,5R)-5-Acetylamino-4-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-pent-2-enoic acid methyl ester
CAS No.:436145-51-6
Molecular Formula:C₂₁H₂₉NO₇
Molecular Weight:407.464
Hs Code.:

Synonyms:(Z)-(4S,5R)-5-Acetylamino-4-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-pent-2-enoic acid methyl ester

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Chemical Property of (Z)-(4S,5R)-5-Acetylamino-4-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-pent-2-enoic acid methyl ester

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Technology Process of (Z)-(4S,5R)-5-Acetylamino-4-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-pent-2-enoic acid methyl ester

There total 4 articles about (Z)-(4S,5R)-5-Acetylamino-4-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-pent-2-enoic acid methyl 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: 30.0%

: 16141-78-9
methyl 2-dimethoxyphosphoryl-2-methoxyacetate

: 436145-50-5
N-[(1S,2R)-2-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-oxo-propyl]-acetamide

: 436145-52-7
(E)-(4S,5R)-5-Acetylamino-4-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-pent-2-enoic acid methyl ester

: 436145-51-6
(Z)-(4S,5R)-5-Acetylamino-4-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-pent-2-enoic acid methyl ester

Guidance literature:: methyl 2-dimethoxyphosphoryl-2-methoxyacetate; With sodium hydride; In tetrahydrofuran; at 25 ℃; for 2h;

N-[(1S,2R)-2-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-oxo-propyl]-acetamide; In tetrahydrofuran; at 0 - 25 ℃; for 5h; Further stages.;
DOI:10.1021/jo020038p

Reference yield:

: 1053645-62-7
N-[(1S,2R)-2-Benzyloxy-1-((R)-1,2-dihydroxy-ethyl)-3-hydroxy-propyl]-acetamide

: 436145-51-6
(Z)-(4S,5R)-5-Acetylamino-4-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-pent-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 0.043 g / PTSA / acetone / 1 h / 25 °C

2.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 3.5 h / -78 - 25 °C

3.1: NaH / tetrahydrofuran / 2 h / 25 °C

3.2: 30 percent / tetrahydrofuran / 5 h / 0 - 25 °C

With oxalyl dichloride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; acetone; 2.1: Swern oxidation;
DOI:10.1021/jo020038p

Reference yield:

: 436145-49-2
N-[(1R,2R)-2-Benzyloxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-hydroxy-propyl]-acetamide

: 436145-51-6
(Z)-(4S,5R)-5-Acetylamino-4-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methoxy-pent-2-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 3.5 h / -78 - 25 °C

2.1: NaH / tetrahydrofuran / 2 h / 25 °C

2.2: 30 percent / tetrahydrofuran / 5 h / 0 - 25 °C

With oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1.1: Swern oxidation;
DOI:10.1021/jo020038p