(S)-2-tert-butoxycarbonylamino-5-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-pent-4-ynoic acid methyl ester

Base Information

Chemical Name:(S)-2-tert-butoxycarbonylamino-5-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-pent-4-ynoic acid methyl ester
CAS No.:499135-05-6
Molecular Formula:C₄₅H₅₁NO₉
Molecular Weight:749.901
Hs Code.:

Synonyms:(S)-2-tert-butoxycarbonylamino-5-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-pent-4-ynoic acid methyl ester

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Chemical Property of (S)-2-tert-butoxycarbonylamino-5-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-pent-4-ynoic acid methyl ester

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Technology Process of (S)-2-tert-butoxycarbonylamino-5-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-pent-4-ynoic acid methyl ester

There total 2 articles about (S)-2-tert-butoxycarbonylamino-5-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-pent-4-ynoic 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: 43.0%

: 93267-04-0,170848-34-7,889670-02-4
N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester

: 139195-57-6
2-iodoethenyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

: 139195-28-1
(2R,3R,4R,5S,6R)-3,4,5-tribenzyloxy-2-(benzyloxymethyl)-6-ethynyltetrahydropyran

: 499135-05-6
(S)-2-tert-butoxycarbonylamino-5-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-pent-4-ynoic acid methyl ester

Guidance literature:: N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester; With chloro-trimethyl-silane; ethylene dibromide; zinc; In tetrahydrofuran; at 40 ℃; for 8h; ultrasound irradiation;

2-iodoethenyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside; With lithium chloride; In tetrahydrofuran; at -78 - 4 ℃;
DOI:10.1271/bbb.66.2273

Reference yield:

: 139195-28-1
(2R,3R,4R,5S,6R)-3,4,5-tribenzyloxy-2-(benzyloxymethyl)-6-ethynyltetrahydropyran

: 499135-05-6
(S)-2-tert-butoxycarbonylamino-5-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-pent-4-ynoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 86 percent / iodine; morpholine / benzene / 24 h / 45 °C

2.1: Zn; 1,2-dibromoethane; TMSCl / tetrahydrofuran / 8 h / 40 °C / ultrasound irradiation

2.2: 43 percent / CuCN; LiCl / tetrahydrofuran / -78 - 4 °C

With morpholine; chloro-trimethyl-silane; iodine; ethylene dibromide; zinc; In tetrahydrofuran; benzene;
DOI:10.1271/bbb.66.2273

Reference yield: 89.0%

: 61613-20-5
N-tosyl-2-iodoaniline

: 499135-05-6
(S)-2-tert-butoxycarbonylamino-5-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-pent-4-ynoic acid methyl ester

: (S)-2-tert-Butoxycarbonylamino-3-[1-(toluene-4-sulfonyl)-3-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1H-indol-2-yl]-propionic acid methyl ester

Guidance literature:: With palladium diacetate; tetrabutyl-ammonium chloride; triphenylphosphine; In N,N-dimethyl-formamide; at 90 ℃; for 16h;
DOI:10.1271/bbb.66.2273