methyl 1-(((3R,4S,E)-6-(((benzyloxy)carbonyl)amino)-4-hydroxy-1-phenylhex-1-en-3-yl)amino)cyclopentanecarboxylate

Base Information

Chemical Name:methyl 1-(((3R,4S,E)-6-(((benzyloxy)carbonyl)amino)-4-hydroxy-1-phenylhex-1-en-3-yl)amino)cyclopentanecarboxylate
CAS No.:1334430-65-7
Molecular Formula:C₂₇H₃₄N₂O₅
Molecular Weight:466.577
Hs Code.:

Synonyms:methyl 1-(((3R,4S,E)-6-(((benzyloxy)carbonyl)amino)-4-hydroxy-1-phenylhex-1-en-3-yl)amino)cyclopentanecarboxylate

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Chemical Property of methyl 1-(((3R,4S,E)-6-(((benzyloxy)carbonyl)amino)-4-hydroxy-1-phenylhex-1-en-3-yl)amino)cyclopentanecarboxylate

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Technology Process of methyl 1-(((3R,4S,E)-6-(((benzyloxy)carbonyl)amino)-4-hydroxy-1-phenylhex-1-en-3-yl)amino)cyclopentanecarboxylate

There total 8 articles about methyl 1-(((3R,4S,E)-6-(((benzyloxy)carbonyl)amino)-4-hydroxy-1-phenylhex-1-en-3-yl)amino)cyclopentanecarboxylate 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: 80.0%

: 1029603-94-8
(E)-diethyl styrylboronate

: 1334430-37-3
benzyl 2-((4S)-5-hydroxy-2,2-dimethyl-1,3-dioxolan-4-yl)ethylcarbamate

: 78388-61-1
cycloleucine methyl ester

: 1334430-65-7
methyl 1-(((3R,4S,E)-6-(((benzyloxy)carbonyl)amino)-4-hydroxy-1-phenylhex-1-en-3-yl)amino)cyclopentanecarboxylate

Guidance literature:: benzyl 2-((4S)-5-hydroxy-2,2-dimethyl-1,3-dioxolan-4-yl)ethylcarbamate; cycloleucine methyl ester; With (R)-3,3'-dibromo-1,1'-bi-2-naphthol; In α,α,α-trifluorotoluene; for 0.0333333h; Inert atmosphere;

(E)-diethyl styrylboronate; In α,α,α-trifluorotoluene; at 20 ℃; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/anie.201103271

Reference yield: 33.0%

: 1029603-94-8
(E)-diethyl styrylboronate

: 1334430-37-3
benzyl 2-((4S)-5-hydroxy-2,2-dimethyl-1,3-dioxolan-4-yl)ethylcarbamate

: 78388-61-1
cycloleucine methyl ester

: benzyl (2-((7S,8S)-10-oxo-7-((E)-styryl)-9-oxa-6-azaspiro[4.5]decan-8-yl)ethyl)carbamate

: 1334430-65-7
methyl 1-(((3R,4S,E)-6-(((benzyloxy)carbonyl)amino)-4-hydroxy-1-phenylhex-1-en-3-yl)amino)cyclopentanecarboxylate

Guidance literature:: benzyl 2-((4S)-5-hydroxy-2,2-dimethyl-1,3-dioxolan-4-yl)ethylcarbamate; cycloleucine methyl ester; With (S)-3,3'-dibromo-1,1'-bi-2-naphthol; In α,α,α-trifluorotoluene; for 0.0333333h; Inert atmosphere; Molecular sieve;

(E)-diethyl styrylboronate; In α,α,α-trifluorotoluene; at 20 ℃; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/anie.201103271

Reference yield:

: 1334430-36-2
(S)-benzyl 2-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)ethylcarbamate

: 1334430-65-7
methyl 1-(((3R,4S,E)-6-(((benzyloxy)carbonyl)amino)-4-hydroxy-1-phenylhex-1-en-3-yl)amino)cyclopentanecarboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium aluminium tetrahydride / tetrahydrofuran / -78 °C / Inert atmosphere

2.1: (R)-3,3'-dibromo-1,1'-bi-2-naphthol / α,α,α-trifluorotoluene / 0.03 h / Inert atmosphere

2.2: 20 °C / Inert atmosphere

With lithium aluminium tetrahydride; (R)-3,3'-dibromo-1,1'-bi-2-naphthol; In tetrahydrofuran; α,α,α-trifluorotoluene; 2.2: Petasis reaction;
DOI:10.1002/anie.201103271