(2S,3R)-3-[1-(2-Acetoxy-1,1-dimethyl-ethyl)-1H-indol-3-yl]-2-benzyloxycarbonylamino-3-hydroxy-propionic acid ethyl ester

Base Information

Chemical Name:(2S,3R)-3-[1-(2-Acetoxy-1,1-dimethyl-ethyl)-1H-indol-3-yl]-2-benzyloxycarbonylamino-3-hydroxy-propionic acid ethyl ester
CAS No.:753487-67-1
Molecular Formula:C₂₇H₃₂N₂O₇
Molecular Weight:496.56
Hs Code.:

Synonyms:(2S,3R)-3-[1-(2-Acetoxy-1,1-dimethyl-ethyl)-1H-indol-3-yl]-2-benzyloxycarbonylamino-3-hydroxy-propionic acid ethyl ester

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Chemical Property of (2S,3R)-3-[1-(2-Acetoxy-1,1-dimethyl-ethyl)-1H-indol-3-yl]-2-benzyloxycarbonylamino-3-hydroxy-propionic acid ethyl ester

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Technology Process of (2S,3R)-3-[1-(2-Acetoxy-1,1-dimethyl-ethyl)-1H-indol-3-yl]-2-benzyloxycarbonylamino-3-hydroxy-propionic acid ethyl ester

There total 3 articles about (2S,3R)-3-[1-(2-Acetoxy-1,1-dimethyl-ethyl)-1H-indol-3-yl]-2-benzyloxycarbonylamino-3-hydroxy-propionic acid ethyl 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:

: acetic acid 2-indol-1-yl-2-methyl-propyl ester

: 753487-67-1
(2S,3R)-3-[1-(2-Acetoxy-1,1-dimethyl-ethyl)-1H-indol-3-yl]-2-benzyloxycarbonylamino-3-hydroxy-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: POCl₃ / 0.5 h / 0 °C

1.2: 90 percent / 1.5 h / 20 °C

2.1: NaH / tetrahydrofuran / 1 h / 20 °C

2.2: 90 percent / tetrahydrofuran / 8 h / 20 °C

3.1: NaOH; K₂[OsO₂(OH)4]; t-butyl hypochlorite / propan-1-ol; H₂O / 0.42 h

3.2: (DHQD)2AQH; K₂[OsO₂(OH)4] / propan-1-ol; H₂O / 3 h

With sodium hydroxide; tert-butylhypochlorite; K2; sodium hydride; trichlorophosphate; In tetrahydrofuran; propan-1-ol; water; 2.2: Wittig reaction / 3.2: Sharpless asymmetric aminohydroxylation;
DOI:10.1021/ol049065n

Reference yield:

: 753488-05-0
acetic acid 2-(3-formyl-indol-1-yl)-2-methyl-propyl ester

: 753487-67-1
(2S,3R)-3-[1-(2-Acetoxy-1,1-dimethyl-ethyl)-1H-indol-3-yl]-2-benzyloxycarbonylamino-3-hydroxy-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 1 h / 20 °C

1.2: 90 percent / tetrahydrofuran / 8 h / 20 °C

2.1: NaOH; K₂[OsO₂(OH)4]; t-butyl hypochlorite / propan-1-ol; H₂O / 0.42 h

2.2: (DHQD)2AQH; K₂[OsO₂(OH)4] / propan-1-ol; H₂O / 3 h

With sodium hydroxide; tert-butylhypochlorite; K2; sodium hydride; In tetrahydrofuran; propan-1-ol; water; 1.2: Wittig reaction / 2.2: Sharpless asymmetric aminohydroxylation;
DOI:10.1021/ol049065n

Reference yield:

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

: 753487-65-9
3-[1-(2-acetoxy-1,1-dimethyl-ethyl)-1H-indol-3-yl]-acrylic acid ethyl ester

: (2R,3S)-3-[1-(2-Acetoxy-1,1-dimethyl-ethyl)-1H-indol-3-yl]-2-benzyloxycarbonylamino-3-hydroxy-propionic acid ethyl ester

: 753487-67-1
(2S,3R)-3-[1-(2-Acetoxy-1,1-dimethyl-ethyl)-1H-indol-3-yl]-2-benzyloxycarbonylamino-3-hydroxy-propionic acid ethyl ester

Guidance literature:: benzyl chloroformate; With sodium hydroxide; tert-butylhypochlorite; K2; In propan-1-ol; water; for 0.416667h;

3-[1-(2-acetoxy-1,1-dimethyl-ethyl)-1H-indol-3-yl]-acrylic acid ethyl ester; With K2; (DHQD)2AQH; In propan-1-ol; water; for 3h; Title compound not separated from byproducts;
DOI:10.1021/ol049065n