sarsasapogenin 3,6-di-O-benzoyl-β-D-glucopyranose

Base Information

• Chemical Name: sarsasapogenin 3,6-di-O-benzoyl-β-D-glucopyranose
• CAS No.: 1186633-13-5
• Molecular Formula: C₄₇H₆₂O₁₀
• Molecular Weight: 787.003
• Mol file: 1186633-13-5.mol

Synonyms:sarsasapogenin 3,6-di-O-benzoyl-β-D-glucopyranose

Chemical Property of sarsasapogenin 3,6-di-O-benzoyl-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of sarsasapogenin 3,6-di-O-benzoyl-β-D-glucopyranose

There total 2 articles about sarsasapogenin 3,6-di-O-benzoyl-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: 67.0%

sarsasapogenin (126-19-2) + 3,6-di-O-benzoylated-isopropyl-β-D-1-thiogalactopyranoside (615570-19-9) → sarsasapogenin 3,6-di-O-benzoyl-β-D-glucopyranose (1186633-13-5)

Guidance literature:

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -42 ℃; for 0.833333h; Under N₂ atmosphere;

DOI:10.1039/b905091d

Reference yield:

isopropyl β-D-thiogalactopyranoside (367-93-1) + benzoyl chloride (98-88-4) → sarsasapogenin 3,6-di-O-benzoyl-β-D-glucopyranose (1186633-13-5)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 0 °C

2: triisopropylsilyl trifluoromethanesulfonate; N-iodo-succinimide / dichloromethane / 1 h / -42 °C / Inert atmosphere

With pyridine; N-iodo-succinimide; triisopropylsilyl trifluoromethanesulfonate; In dichloromethane;

Reference yield: 90.0%

sarsasapogenin 3,6-di-O-benzoyl-β-D-glucopyranose (1186633-13-5) → sarsasapogenin-3-O-β-galactopyranoside (68422-00-4)

Guidance literature:

With methanol; sodium methylate; In dichloromethane; at 20 ℃; for 3.5h;

upstream raw materials:

sarsasapogenin

3,6-di-O-benzoylated-isopropyl-β-D-1-thiogalactopyranoside

isopropyl β-D-thiogalactopyranoside

benzoyl chloride

Downstream raw materials:

sarsasapogenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->2)-3,6-di-O-benzoyl-β-D-galactopyranoside

sarsasapogenin-3-O-β-galactopyranoside

Refernces

• 1、 Cheng, Shuihong,Du, Yuguo,Ma, Baiping,Tan, Dawei. "Total synthesis of a furostan saponin, timosaponin BII". experimental part. p. 3112 - 3118. Retrieved 2011/02/26.