1-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-2-benzyloxy-4-bromomethylbenzene

Base Information

Chemical Name:1-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-2-benzyloxy-4-bromomethylbenzene
CAS No.:444150-26-9
Molecular Formula:C₄₉H₄₉BrO₆
Molecular Weight:813.828
Hs Code.:

Synonyms:1-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-2-benzyloxy-4-bromomethylbenzene

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Chemical Property of 1-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-2-benzyloxy-4-bromomethylbenzene

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Technology Process of 1-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-2-benzyloxy-4-bromomethylbenzene

There total 11 articles about 1-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-2-benzyloxy-4-bromomethylbenzene 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: 82.0%

: 444150-24-7
1-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-2-benzyloxy-4-hydroxymethylbenzene

: 444150-26-9
1-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-2-benzyloxy-4-bromomethylbenzene

Guidance literature:: With N-Bromosuccinimide; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 2h;
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

: 444150-26-9
1-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-2-benzyloxy-4-bromomethylbenzene

Guidance literature:: Multi-step reaction with 10 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

9.1: 89 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

10.1: 82 percent / NBS; PPh₃ / tetrahydrofuran / 2 h / 20 °C

With manganese(IV) oxide; N-Bromosuccinimide; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; chloroformic acid ethyl ester; diisobutylaluminium hydride; potassium carbonate; ozone; triethylamine; triphenylphosphine; 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:

: 100-39-0
benzyl bromide

: 444150-26-9
1-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-2-benzyloxy-4-bromomethylbenzene

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / K₂CO₃ / acetone / 12 h

2: 89 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

3: 82 percent / NBS; PPh₃ / tetrahydrofuran / 2 h / 20 °C

With N-Bromosuccinimide; lithium aluminium tetrahydride; potassium carbonate; triphenylphosphine; In tetrahydrofuran; acetone;
DOI:10.1002/1521-3765(20020415)8:8<1872::AID-CHEM1872>3.0.CO;2-A