2-acetamido-2-[3-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)benzyl]malonic diethyl ester

Base Information

Chemical Name:2-acetamido-2-[3-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)benzyl]malonic diethyl ester
CAS No.:444150-28-1
Molecular Formula:C₅₈H₆₃NO₁₁
Molecular Weight:950.138
Hs Code.:

Synonyms:2-acetamido-2-[3-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)benzyl]malonic diethyl ester

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Chemical Property of 2-acetamido-2-[3-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)benzyl]malonic diethyl ester

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Technology Process of 2-acetamido-2-[3-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)benzyl]malonic diethyl ester

There total 12 articles about 2-acetamido-2-[3-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)benzyl]malonic diethyl 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%

: 1068-90-2
2-acetylaminomalonic acid diethyl ester

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

: 444150-28-1
2-acetamido-2-[3-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)benzyl]malonic diethyl ester

Guidance literature:: 2-acetylaminomalonic acid diethyl ester; With sodium hydride; In N,N-dimethyl-formamide; for 0.333333h;

1-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)-2-benzyloxy-4-bromomethylbenzene; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Further stages.;
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

: 444150-28-1
2-acetamido-2-[3-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)benzyl]malonic diethyl ester

Guidance literature:: Multi-step reaction with 11 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

11.1: NaH / dimethylformamide / 0.33 h

11.2: 69 percent / dimethylformamide / 2 h / 20 °C

With manganese(IV) oxide; N-Bromosuccinimide; lithium aluminium tetrahydride; boron trifluoride diethyl etherate; chloroformic acid ethyl ester; sodium hydride; diisobutylaluminium hydride; potassium carbonate; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 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

: 444150-28-1
2-acetamido-2-[3-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranos-1-ylmethyl)benzyl]malonic diethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 85 percent / K₂CO₃ / acetone / 12 h

2.1: 89 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

3.1: 82 percent / NBS; PPh₃ / tetrahydrofuran / 2 h / 20 °C

4.1: NaH / dimethylformamide / 0.33 h

4.2: 69 percent / dimethylformamide / 2 h / 20 °C

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