1,6-di-O-acetyl-3-O-allyloxycarbonyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-α-D-glucopyranose

Base Information

• Chemical Name: 1,6-di-O-acetyl-3-O-allyloxycarbonyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-α-D-glucopyranose
• CAS No.: 919081-74-6
• Molecular Formula: C₃₁H₃₆O₁₂
• Molecular Weight: 600.62
• Mol file: 919081-74-6.mol

Synonyms:1,6-di-O-acetyl-3-O-allyloxycarbonyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-α-D-glucopyranose

Chemical Property of 1,6-di-O-acetyl-3-O-allyloxycarbonyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-α-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-di-O-acetyl-3-O-allyloxycarbonyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-α-D-glucopyranose

There total 4 articles about 1,6-di-O-acetyl-3-O-allyloxycarbonyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-α-D-glucopyranose 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: 98.0%

1,6-anhydro-3-O-allyloxycarbonyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-β-D-glucopyranose (919081-72-4) + acetic anhydride (108-24-7) → 1,6-di-O-acetyl-3-O-allyloxycarbonyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-α-D-glucopyranose (919081-74-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; at 0 ℃; for 0.5h;

DOI:10.1002/ejoc.200600440

Reference yield:

1,6-anhydro-4-O-benzyl-2-O-[(S)-α-(ethoxycarbonyl)benzyl]-β-D-glucopyranose (849619-42-7) → 1,6-di-O-acetyl-3-O-allyloxycarbonyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-α-D-glucopyranose (919081-74-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / tetramethyl ethylenediamine / CH₂Cl₂ / 2 h / 20 °C

2: 98 percent / trimethylsilyl trifluoromethanesulfonate / 0.5 h / 0 °C

With N,N,N,N,-tetramethylethylenediamine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane;

DOI:10.1002/ejoc.200600440

Reference yield:

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose (33208-47-8) → 1,6-di-O-acetyl-3-O-allyloxycarbonyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-α-D-glucopyranose (919081-74-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 48 percent / BF₃*OEt₂; 4 Angstroem molecular sieves / toluene / 1 h / 20 °C

2: 87 percent / tetramethyl ethylenediamine / CH₂Cl₂ / 2 h / 20 °C

3: 98 percent / trimethylsilyl trifluoromethanesulfonate / 0.5 h / 0 °C

With N,N,N,N,-tetramethylethylenediamine; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane; toluene;

DOI:10.1002/ejoc.200600440

upstream raw materials:

1,6-anhydro-3-O-allyloxycarbonyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-β-D-glucopyranose

acetic anhydride

1,6-anhydro-4-O-benzyl-2-O-[(S)-α-(ethoxycarbonyl)benzyl]-β-D-glucopyranose

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose

Downstream raw materials:

6-O-acetyl-3-O-allyloxycarbonyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-α-D-glucopyranosyl trichloroacetimidate