(-)-menthyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside

Base Information

• Chemical Name: (-)-menthyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside
• CAS No.: 124673-17-2
• Molecular Formula: C₃₆H₅₄O₁₈
• Molecular Weight: 774.814
• Mol file: 124673-17-2.mol

Synonyms:(-)-menthyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside

Chemical Property of (-)-menthyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-menthyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside

There total 3 articles about (-)-menthyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside 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: 83.0%

(-)-menthol (2216-51-5) + 2,4,6-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranosyl trichloroacetimidate (888945-73-1) → (-)-menthyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside (124673-17-2)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; for 2h; Inert atmosphere;

DOI:10.1016/j.bmcl.2012.04.035

Reference yield:

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl (1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranoside (18423-99-9,54269-49-7) → (-)-menthyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside (124673-17-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / Inert atmosphere

2: boron trifluoride diethyl etherate / dichloromethane / 2 h / Inert atmosphere

With boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

DOI:10.1016/j.bmcl.2012.04.035

Reference yield:

gentibiose (536-11-8,645-03-4,902-54-5,3031-35-4,4604-26-6,5340-95-4,5995-99-3,5996-00-9,13299-20-2,13299-21-3,15548-40-0,16750-26-8,16967-97-8,23339-29-9,24822-33-1,33428-65-8,34674-94-7,35867-21-1,37169-69-0,37169-72-5,38533-27-6,50271-70-0,65207-30-9,82729-73-5,95463-59-5,100427-99-4,100430-37-3,100483-14-5,102572-70-3,110658-40-7,123809-47-2,140461-60-5,143615-15-0) → (-)-menthyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside (124673-17-2)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine; dmap / 24 h / Inert atmosphere

2: morpholine / dichloromethane / 2 h / Inert atmosphere; Reflux

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / Inert atmosphere

4: boron trifluoride diethyl etherate / dichloromethane / 2 h / Inert atmosphere

With morpholine; pyridine; dmap; boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;

DOI:10.1016/j.bmcl.2012.04.035

upstream raw materials:

gentibiose

2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl (1->6)-2,3,4-tri-O-acetyl-β-D-glucopyranoside

(-)-menthol

2,4,6-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranosyl trichloroacetimidate