Methyl 2,3-O-Carbonyl-4,6-O-isopropylidene-a-D-mannopyranoside

Base Information

• Chemical Name: Methyl 2,3-O-Carbonyl-4,6-O-isopropylidene-a-D-mannopyranoside
• CAS No.: 74948-73-5
• Molecular Formula: C₁₁H₁₆O₇
• Molecular Weight: 260.244
• Mol file: 74948-73-5.mol

Synonyms:1,3-Dioxolo[4,5]pyrano[3,2-d][1,3]dioxin,a-D-mannopyranoside deriv.

Chemical Property of Methyl 2,3-O-Carbonyl-4,6-O-isopropylidene-a-D-mannopyranoside

Chemical Property:

• PSA: 72.45000
• LogP: 0.41320
• Solubility.: Methanol

Purity/Quality:

98% ^*data from raw suppliers

Methyl2,3-O-Carbonyl-4,6-O-isopropylidene-α-D-mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Used for the synthesis of a-mannosides Methyl 2,3-O-Carbonyl-4,6-O-isopropylidene-a-D-mannopyranoside is used for the synthesis of α-mannosides.

Technology Process of Methyl 2,3-O-Carbonyl-4,6-O-isopropylidene-a-D-mannopyranoside

There total 6 articles about Methyl 2,3-O-Carbonyl-4,6-O-isopropylidene-a-D-mannopyranoside 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: 86.0%

methyl 4,6-O-isopropylidene-α-D-mannopyranoside (63167-67-9) + 1,1'-Thiocarbonyldiimidazole (6160-65-2) → methyl 2,3-O-carbonyl-4,6-O-isopropylidene-α-D-mannopyranoside (74948-73-5)

Guidance literature:

In tetrahydrofuran; for 4h;

Reference yield: 82.0%

methyl 4,6-O-isopropylidene-α-D-mannopyranoside (63167-67-9) + dichloromethylenedimethyliminium chloride (33842-02-3,529510-96-1) → methyl 2,3-O-carbonyl-4,6-O-isopropylidene-α-D-mannopyranoside (74948-73-5)

Guidance literature:

With pyridine; at 25 ℃; for 5h;

Reference yield: 78.0%

methyl 4,6-O-isopropylidene-2,3-O-thiocarbonyl-α-D-mannoside (74948-68-8) → methyl 2,3-O-carbonyl-4,6-O-isopropylidene-α-D-mannopyranoside (74948-73-5)

Guidance literature:

With methyloxirane; methyl iodide; at 80 ℃; for 14h;

upstream raw materials:

methyl 4,6-O-isopropylidene-α-D-mannopyranoside

dichloromethylenedimethyliminium chloride

methyl 4,6-O-isopropylidene-2,3-O-thiocarbonyl-α-D-mannoside

methyl chloroformate

Downstream raw materials:

4,6-di-O-acetyl-2,3-O-carbonyl-α-D-mannopyranosyl bromide

(2S,3S,4S,5S,6R)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol

1,4,6-tri-O-acetyl-2,3-O-carbonyl-α-D-mannopyranose

1,4,6-tri-O-acetyl-2,3-O-carbonyl-β-D-mannopyranose

Refernces

• 1、 Patroni, Joseph J.,Skelton, Brian W.,Stick, Robert V.,White, Allan H.. "The Reaction of Methyl 4,6-O-Isopropylidene-2,3-O-thiocarbonyl-α-D-mannoside with Methyl Iodide: a Synthesis of Methyl α-Tyveloside (Methyl 3,6-Dideoxy-α-D-arabino-hexopyranoside)". . p. 987 - 999. Retrieved 2007/10/02.