2-acetamido-2-[3-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-β-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-β-D-glucopyranos-1-ylmethyl)benzyl]malonic diethyl ester
• CAS No.: 444150-29-2
• Molecular Formula: C₅₈H₆₃NO₁₁
• Molecular Weight: 950.138
• Mol file: 444150-29-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-acetamido-2-[3-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-β-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-β-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: 65.0%

2-acetylaminomalonic acid diethyl ester (1068-90-2) + 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-ylmethyl)-2-benzyloxy-4-bromomethylbenzene (444150-27-0) → 2-acetamido-2-[3-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-ylmethyl)benzyl]malonic diethyl ester (444150-29-2)

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-β-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:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → 2-acetamido-2-[3-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-ylmethyl)benzyl]malonic diethyl ester (444150-29-2)

Guidance literature:

Multi-step reaction with 12 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

5.1: 88 percent / DIBAL / toluene / -78 - 25 °C

6.1: MnO₂ / CH₂Cl₂ / 3 h / Heating

7.1: 13.3 g / CH₂Cl₂ / 3 h / Heating

8.1: 65 percent / ethyl chloroformate; Et₃N / tetrahydrofuran / 0.5 h / 20 °C

9.1: 87 percent / K₂CO₃ / acetone / 12 h

10.1: 91 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

11.1: 79 percent / NBS; PPh₃ / tetrahydrofuran / 2 h / 20 °C

12.1: NaH / dimethylformamide / 0.33 h

12.2: 65 percent / dimethylformamide / 2 h / 20 °C

With triethylsilane; 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; 4.1: Wittig reaction / 7.1: Wittig reaction;

DOI:10.1002/1521-3765(20020415)8:8<1872::AID-CHEM1872>3.0.CO;2-A

Reference yield:

2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3) → 2-acetamido-2-[3-benzyloxy-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-ylmethyl)benzyl]malonic diethyl ester (444150-29-2)

Guidance literature:

Multi-step reaction with 13 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

6.1: 88 percent / DIBAL / toluene / -78 - 25 °C

7.1: MnO₂ / CH₂Cl₂ / 3 h / Heating

8.1: 13.3 g / CH₂Cl₂ / 3 h / Heating

9.1: 65 percent / ethyl chloroformate; Et₃N / tetrahydrofuran / 0.5 h / 20 °C

10.1: 87 percent / K₂CO₃ / acetone / 12 h

11.1: 91 percent / LiAlH₄ / tetrahydrofuran / 1 h / 20 °C

12.1: 79 percent / NBS; PPh₃ / tetrahydrofuran / 2 h / 20 °C

13.1: NaH / dimethylformamide / 0.33 h

13.2: 65 percent / dimethylformamide / 2 h / 20 °C

With triethylsilane; manganese(IV) oxide; N-Bromosuccinimide; lithium aluminium tetrahydride; jones reagent; 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; 5.1: Wittig reaction / 8.1: Wittig reaction;

DOI:10.1002/1521-3765(20020415)8:8<1872::AID-CHEM1872>3.0.CO;2-A

upstream raw materials:

2-acetylaminomalonic acid diethyl ester

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

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

2,3,4,6-tetra-O-benzyl-D-glucopyranose

Downstream raw materials:

(S)-2-Amino-3-[3-benzyloxy-4-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-propionic acid