(2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-((R)-2-benzyloxycarbonylamino-3-methylbutyrylamino)-(tert-butoxycarbonylmethylcarbamoy)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

Base Information

Chemical Name:(2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-((R)-2-benzyloxycarbonylamino-3-methylbutyrylamino)-(tert-butoxycarbonylmethylcarbamoy)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester
CAS No.:870137-22-7
Molecular Formula:C₅₄H₆₆N₄O₁₃
Molecular Weight:979.137
Hs Code.:

(2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-((R)-2-benzyloxycarbonylamino-3-methylbutyrylamino)-(tert-butoxycarbonylmethylcarbamoy)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

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Chemical Property of (2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-((R)-2-benzyloxycarbonylamino-3-methylbutyrylamino)-(tert-butoxycarbonylmethylcarbamoy)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

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Technology Process of (2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-((R)-2-benzyloxycarbonylamino-3-methylbutyrylamino)-(tert-butoxycarbonylmethylcarbamoy)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

There total 11 articles about (2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-((R)-2-benzyloxycarbonylamino-3-methylbutyrylamino)-(tert-butoxycarbonylmethylcarbamoy)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl 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:

: 870137-16-9
{[(2S,3S)-3-ethynyl-3-methyl-1-(2-nitrobenzenesulfonyl)-aziridine-2-carbonyl]amino}acetic acid tert-butyl ester

: 870137-22-7
(2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-((R)-2-benzyloxycarbonylamino-3-methylbutyrylamino)-(tert-butoxycarbonylmethylcarbamoy)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / CuOAc; DBU / toluene

2: 78 percent / PhSH; Cs₂CO₃ / dimethylformamide

3: 97 percent / EDCI*HCl; HOBt; NaHCO₃ / dimethylformamide

With copper (I) acetate; sodium hydrogencarbonate; benzotriazol-1-ol; caesium carbonate; thiophenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmcl.2006.06.071

Reference yield:

: 870137-17-0
(2S,3R)-3-(4-benzyloxy-3-hydroxyphenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

: 870137-22-7
(2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-((R)-2-benzyloxycarbonylamino-3-methylbutyrylamino)-(tert-butoxycarbonylmethylcarbamoy)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / CuOAc; DBU / toluene

2: 78 percent / PhSH; Cs₂CO₃ / dimethylformamide

3: 97 percent / EDCI*HCl; HOBt; NaHCO₃ / dimethylformamide

With copper (I) acetate; sodium hydrogencarbonate; benzotriazol-1-ol; caesium carbonate; thiophenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmcl.2006.06.071

Reference yield:

: 821006-11-5
(4S,5R)-3-(3-acetoxy-4-benzyloxyphenyl)-3-hydroxy-2-methylaminopropionic acid methyl ester

: 870137-22-7
(2S,3R)-3-(4-benzyloxy-3-{(R)-1-[(S)-((R)-2-benzyloxycarbonylamino-3-methylbutyrylamino)-(tert-butoxycarbonylmethylcarbamoy)methyl]-1-methylprop-2-ynyloxy}phenyl)-2-(tert-butoxycarbonylmethylamino)-3-hydroxypropionic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: aq.LiOH

2: DBU

3: 90 percent / CuOAc; DBU / toluene / 2 h / 0 °C

4: 78 percent / PhSH; Cs₂CO₃ / dimethylformamide / 5 h / 20 °C

5: 97 percent / EDCI*HCl; HOBT; NaHCO₃ / dimethylformamide / 24 h / 20 °C

With lithium hydroxide; copper (I) acetate; sodium hydrogencarbonate; benzotriazol-1-ol; caesium carbonate; thiophenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol052287g