4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-3-hydroxybenzoic ethyl ester

Base Information

Chemical Name:4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-3-hydroxybenzoic ethyl ester
CAS No.:444150-20-3
Molecular Formula:C₄₄H₄₆O₈
Molecular Weight:702.844
Hs Code.:

Synonyms:4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-3-hydroxybenzoic ethyl ester

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Chemical Property of 4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-3-hydroxybenzoic ethyl ester

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Technology Process of 4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-3-hydroxybenzoic ethyl ester

There total 7 articles about 4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-3-hydroxybenzoic 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: 69.0%

: 444150-18-9
7-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-yl)-3-ethoxycarbonyl-hepta-3,5-dienoic acid

: 444150-20-3
4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-3-hydroxybenzoic ethyl ester

Guidance literature:: With chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; at 20 ℃; for 0.5h;
DOI:10.1002/1521-3765(20020415)8:8<1872::AID-CHEM1872>3.0.CO;2-A

Reference yield:

: 80300-30-7
1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose

: 444150-20-3
4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-3-hydroxybenzoic ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 89 percent / BF₃*OEt₂ / acetonitrile / 24 h / 4 °C

2.1: ozone / CH₂Cl₂; methanol / -78 °C

2.2: PPh₃

3.1: 24.3 g / toluene / 2 h / Heating

4.1: 86 percent / DIBAL / toluene / -78 - 25 °C

5.1: MnO₂ / CH₂Cl₂ / 3 h / Heating

6.1: 14.7 g / CH₂Cl₂ / 3 h / Heating

7.1: 69 percent / ethyl chloroformate; Et₃N / tetrahydrofuran / 0.5 h / 20 °C

With manganese(IV) oxide; boron trifluoride diethyl etherate; chloroformic acid ethyl ester; diisobutylaluminium hydride; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile; 3.1: Wittig reaction / 6.1: Wittig reaction;
DOI:10.1002/1521-3765(20020415)8:8<1872::AID-CHEM1872>3.0.CO;2-A

Reference yield:

: 87256-50-6
4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-yl)-but-2-en-1-ol

: 444150-20-3
4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-3-hydroxybenzoic ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: MnO₂ / CH₂Cl₂ / 3 h / Heating

2: 14.7 g / CH₂Cl₂ / 3 h / Heating

3: 69 percent / ethyl chloroformate; Et₃N / tetrahydrofuran / 0.5 h / 20 °C

With manganese(IV) oxide; chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; dichloromethane; 2: Wittig reaction;
DOI:10.1002/1521-3765(20020415)8:8<1872::AID-CHEM1872>3.0.CO;2-A