N-[4-(hydroxymethyl)phenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate

Base Information

Chemical Name:N-[4-(hydroxymethyl)phenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate
CAS No.:186653-58-7
Molecular Formula:C₂₁H₂₅NO₁₂
Molecular Weight:483.429
Hs Code.:

Synonyms:N-[4-(hydroxymethyl)phenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate

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Chemical Property of N-[4-(hydroxymethyl)phenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate

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Technology Process of N-[4-(hydroxymethyl)phenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate

There total 9 articles about N-[4-(hydroxymethyl)phenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate 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: 92.0%

: 184579-83-7
N-[4-(t-butyldimethylsilyloxymethyl)phenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate

: 186653-58-7
N-[4-(hydroxymethyl)phenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate

Guidance literature:: With water; acetic acid; In tetrahydrofuran; for 3h;
DOI:10.1016/S0968-0896(99)00095-4

Reference yield:

: 104292-83-3
4-<(tert-butyldimethylsiloxy)methyl>benzoic acid

: 186653-58-7
N-[4-(hydroxymethyl)phenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate

Guidance literature:: Multi-step reaction with 2 steps

1: DPPA; Et₃N / 21 h / 20 - 80 °C

2: HOAc; H₂O / tetrahydrofuran / 2 h / 20 °C

With diphenyl-phosphinic acid; water; acetic acid; triethylamine; In tetrahydrofuran; 1: modified Curtius reaction;
DOI:10.1016/j.bcp.2004.08.004

Reference yield:

: 3082-95-9,72692-06-9,73464-50-3
2,3,4-Tri-O-acetyl-β-D-glucopyranuronic acid methylester

: 186653-58-7
N-[4-(hydroxymethyl)phenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate

Guidance literature:: Multi-step reaction with 2 steps

1: DPPA; Et₃N / 21 h / 20 - 80 °C

2: HOAc; H₂O / tetrahydrofuran / 2 h / 20 °C

With diphenyl-phosphinic acid; water; acetic acid; triethylamine; In tetrahydrofuran; 1: modified Curtius reaction;
DOI:10.1016/j.bcp.2004.08.004