4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-but-2-enoic ethyl ester

Base Information

Chemical Name:4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-but-2-enoic ethyl ester
CAS No.:444150-16-7
Molecular Formula:C₄₀H₄₄O₇
Molecular Weight:636.785
Hs Code.:

Synonyms:4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-but-2-enoic ethyl ester

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Chemical Property of 4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-but-2-enoic ethyl ester

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Technology Process of 4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-but-2-enoic ethyl ester

There total 4 articles about 4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-but-2-enoic 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:

: 13096-62-3
(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

: 444150-16-7
4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-but-2-enoic ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 91 percent / tetrahydrofuran / 2 h / -78 °C

2.1: 78 percent / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 12 h / -78 °C

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

3.2: PPh₃

4.1: 22.9 g / toluene / 2 h / Heating

With triethylsilane; boron trifluoride diethyl etherate; ozone; In tetrahydrofuran; methanol; dichloromethane; toluene; 4.1: Wittig reaction;
DOI:10.1002/1521-3765(20020415)8:8<1872::AID-CHEM1872>3.0.CO;2-A

Reference yield:

: 6564-72-3
2,3,4,6-tetra-O-benzyl-D-glucopyranose

: 444150-16-7
4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-but-2-enoic ethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: Jones reagent / acetone

2.1: 91 percent / tetrahydrofuran / 2 h / -78 °C

3.1: 78 percent / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 12 h / -78 °C

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

4.2: PPh₃

5.1: 22.9 g / toluene / 2 h / Heating

With triethylsilane; jones reagent; boron trifluoride diethyl etherate; ozone; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene; 5.1: Wittig reaction;
DOI:10.1002/1521-3765(20020415)8:8<1872::AID-CHEM1872>3.0.CO;2-A

Reference yield:

: 776313-98-5
5,6,7,9-tetra-O-benzyl-1,2,3-trideoxy-D-gluco-non-1-eno-4-ulopyranose

: 444150-16-7
4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-but-2-enoic ethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 78 percent / Et₃SiH; BF₃*OEt₂ / CH₂Cl₂ / 12 h / -78 °C

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

2.2: PPh₃

3.1: 22.9 g / toluene / 2 h / Heating

With triethylsilane; boron trifluoride diethyl etherate; ozone; In methanol; dichloromethane; toluene; 3.1: Wittig reaction;
DOI:10.1002/1521-3765(20020415)8:8<1872::AID-CHEM1872>3.0.CO;2-A