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

Base Information

• Chemical Name: 1,6-anhydro-3-O-benzoyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-β-D-glucopyranose
• CAS No.: 919081-63-3
• Molecular Formula: C₃₀H₃₀O₈
• Molecular Weight: 518.563
• Mol file: 919081-63-3.mol

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

Chemical Property of 1,6-anhydro-3-O-benzoyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6-anhydro-3-O-benzoyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-β-D-glucopyranose

There total 3 articles about 1,6-anhydro-3-O-benzoyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-β-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: 95.0%

1,6-anhydro-4-O-benzyl-2-O-[(S)-α-(ethoxycarbonyl)benzyl]-β-D-glucopyranose (849619-42-7) + benzoyl chloride (98-88-4) → 1,6-anhydro-3-O-benzoyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-β-D-glucopyranose (919081-63-3)

Guidance literature:

With N,N,N,N,-tetramethylethylenediamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1002/ejoc.200600440

Reference yield:

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose (33208-47-8) → 1,6-anhydro-3-O-benzoyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-β-D-glucopyranose (919081-63-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 95 percent / tetramethyl ethylenediamine / CH₂Cl₂ / 0 - 20 °C

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

DOI:10.1002/ejoc.200600440

Reference yield:

(S)-(-)-ethyl mandelate (13704-09-1) → 1,6-anhydro-3-O-benzoyl-4-O-benzyl-2-O-[(S)-ethoxycarbonylbenzyl]-β-D-glucopyranose (919081-63-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 95 percent / tetramethyl ethylenediamine / CH₂Cl₂ / 0 - 20 °C

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

DOI:10.1002/ejoc.200600440

upstream raw materials:

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

benzoyl chloride

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

(S)-(-)-ethyl mandelate