methyl (R)-(+)-3-((2R,3S,4S,5S)-5-azido-2,3,4,6-tetrakis(benzyloxy)-hexanoylamino)-3-phenylpropionate

Base Information

Chemical Name:methyl (R)-(+)-3-((2R,3S,4S,5S)-5-azido-2,3,4,6-tetrakis(benzyloxy)-hexanoylamino)-3-phenylpropionate
CAS No.:682153-45-3
Molecular Formula:C₄₄H₄₆N₄O₇
Molecular Weight:742.872
Hs Code.:

Synonyms:methyl (R)-(+)-3-((2R,3S,4S,5S)-5-azido-2,3,4,6-tetrakis(benzyloxy)-hexanoylamino)-3-phenylpropionate

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Chemical Property of methyl (R)-(+)-3-((2R,3S,4S,5S)-5-azido-2,3,4,6-tetrakis(benzyloxy)-hexanoylamino)-3-phenylpropionate

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Technology Process of methyl (R)-(+)-3-((2R,3S,4S,5S)-5-azido-2,3,4,6-tetrakis(benzyloxy)-hexanoylamino)-3-phenylpropionate

There total 6 articles about methyl (R)-(+)-3-((2R,3S,4S,5S)-5-azido-2,3,4,6-tetrakis(benzyloxy)-hexanoylamino)-3-phenylpropionate 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:

: 37088-67-8
methyl (3R)-3-amino-3-phenylpropanoate

: (2R,3S,4S,5S)-(+)-5-azido-2,3,4,6-tetrakis(benzyloxy)hexanoic acid

: 682153-45-3
methyl (R)-(+)-3-((2R,3S,4S,5S)-5-azido-2,3,4,6-tetrakis(benzyloxy)-hexanoylamino)-3-phenylpropionate

Guidance literature:: methyl (3R)-3-amino-3-phenylpropanoate; (2R,3S,4S,5S)-(+)-5-azido-2,3,4,6-tetrakis(benzyloxy)hexanoic acid; With benzotriazol-1-ol; In dichloromethane; for 0.0333333h; cooling;

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 10h;
DOI:10.1007/s00706-003-0094-1

Reference yield:

: 82598-84-3
2,3,4,6-tetra-O-benzyl-D-galactonolactone

: 682153-45-3
methyl (R)-(+)-3-((2R,3S,4S,5S)-5-azido-2,3,4,6-tetrakis(benzyloxy)-hexanoylamino)-3-phenylpropionate

Guidance literature:: Multi-step reaction with 6 steps

1.1: aq. LiOH / tetrahydrofuran / 0 °C

1.2: aq. HCl / tetrahydrofuran / pH 2 - 3

2.1: 460 mg / diethyl ether / 20 °C

3.1: 90 percent / Et₃N / CH₂Cl₂ / 0 °C

4.1: 80 percent / NaN₃ / dimethylformamide / 110 °C

5.1: aq. KOH / dioxane / 20 °C

6.1: HOBt / CH₂Cl₂ / 0.03 h / cooling

6.2: 190 mg / EDCI / CH₂Cl₂ / 10 h / 20 °C

With potassium hydroxide; lithium hydroxide; sodium azide; benzotriazol-1-ol; triethylamine; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1007/s00706-003-0094-1

Reference yield:

: (2R,3S,4S,5R)-(+)-2,3,4,6-tetrakis(benzyloxy)-5-hydroxy-hexanoic acid

: 682153-45-3
methyl (R)-(+)-3-((2R,3S,4S,5S)-5-azido-2,3,4,6-tetrakis(benzyloxy)-hexanoylamino)-3-phenylpropionate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 460 mg / diethyl ether / 20 °C

2.1: 90 percent / Et₃N / CH₂Cl₂ / 0 °C

3.1: 80 percent / NaN₃ / dimethylformamide / 110 °C

4.1: aq. KOH / dioxane / 20 °C

5.1: HOBt / CH₂Cl₂ / 0.03 h / cooling

5.2: 190 mg / EDCI / CH₂Cl₂ / 10 h / 20 °C

With potassium hydroxide; sodium azide; benzotriazol-1-ol; triethylamine; In 1,4-dioxane; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1007/s00706-003-0094-1