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

Base Information

Chemical Name:4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-3-benzyloxybenzoic ethyl ester
CAS No.:444150-22-5
Molecular Formula:C₅₁H₅₂O₈
Molecular Weight:792.969
Hs Code.:

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

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

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

There total 8 articles about 4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-3-benzyloxybenzoic 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: 85.0%

: 100-39-0
benzyl bromide

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

: 444150-22-5
4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-3-benzyloxybenzoic ethyl ester

Guidance literature:: With potassium carbonate; In acetone; for 12h;
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

: 444150-22-5
4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-3-benzyloxybenzoic ethyl ester

Guidance literature:: Multi-step reaction with 8 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

8.1: 85 percent / K₂CO₃ / acetone / 12 h

With manganese(IV) oxide; boron trifluoride diethyl etherate; chloroformic acid ethyl ester; diisobutylaluminium hydride; potassium carbonate; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; acetone; 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

: 444150-22-5
4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-3-benzyloxybenzoic ethyl ester

Guidance literature:: Multi-step reaction with 4 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

4: 85 percent / K₂CO₃ / acetone / 12 h

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