3,4,6-tri-O-acetyl-1,2-O-[1-(propan-2-yloxy)ethylidene]hexopyranose

Base Information

• Chemical Name: 3,4,6-tri-O-acetyl-1,2-O-[1-(propan-2-yloxy)ethylidene]hexopyranose
• CAS No.: 20672-70-2
• Molecular Formula: C₁₇H₂₆O₁₀
• Molecular Weight: 390.387
• Mol file: 20672-70-2.mol

Synonyms:Mannopyranose,cyclic 1,2-(isopropyl orthoacetate) 3,4,6-triacetate, b-D- (8CI); 5H-1,3-Dioxolo[4,5-b]pyran,b-D-mannopyranose deriv.;Orthoacetic acid, cyclic ester with b-D-mannopyranose 3,4,6-triacetate, isopropyl ester;NSC 268931

Chemical Property of 3,4,6-tri-O-acetyl-1,2-O-[1-(propan-2-yloxy)ethylidene]hexopyranose

Chemical Property:

• Vapor Pressure: 5.92E-08mmHg at 25°C
• Boiling Point: 440.4°C at 760 mmHg
• Flash Point: 190.2°C
• Density: 1.26g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,4,6-tri-O-acetyl-1,2-O-[1-(propan-2-yloxy)ethylidene]hexopyranose

There total 6 articles about 3,4,6-tri-O-acetyl-1,2-O-[1-(propan-2-yloxy)ethylidene]hexopyranose 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: 66.0%

2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide (572-09-8,3068-32-4,4026-32-8,6919-96-6,13242-53-0,14227-54-4,14795-18-7,19186-59-5,19285-38-2,21698-13-5,29907-26-4,53369-42-9,60619-58-1,61303-35-3,67337-79-5,69127-37-3,70749-15-4,72002-90-5,75247-30-2,75880-74-9,78418-57-2,102339-89-9,102339-90-2,103530-40-1,114028-03-4,114718-45-5,138514-70-2,138514-71-3) + N,N-dimethylformamide diisopropyl acetal (18503-89-4) → Acetic acid (3aS,5R,6R,7S,7aS)-6-acetoxy-5-acetoxymethyl-2-isopropoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-yl ester (20672-70-2)

Guidance literature:

With silver trifluoromethanesulfonate; In dichloromethane; at -10 ℃; for 0.25h;

DOI:10.1021/jo00352a012

Reference yield: 66.0%

2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide (572-09-8,3068-32-4,4026-32-8,6919-96-6,13242-53-0,14227-54-4,14795-18-7,19186-59-5,19285-38-2,21698-13-5,29907-26-4,53369-42-9,60619-58-1,61303-35-3,67337-79-5,69127-37-3,70749-15-4,72002-90-5,75247-30-2,75880-74-9,78418-57-2,102339-89-9,102339-90-2,103530-40-1,114028-03-4,114718-45-5,138514-70-2,138514-71-3) + isopropyl alcohol (67-63-0,8013-70-5) → Acetic acid (3aS,5R,6R,7S,7aS)-6-acetoxy-5-acetoxymethyl-2-isopropoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-yl ester (20672-70-2)

Guidance literature:

With lutidine; tetrabutylammomium bromide; In chloroform; at 45 ℃; for 24h;

DOI:10.1021/jo00352a012

Reference yield:

→ Acetic acid (3aS,5R,6R,7S,7aS)-6-acetoxy-5-acetoxymethyl-2-isopropoxy-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-yl ester (20672-70-2)

Guidance literature:

Tetra-O-acetyl-α-D-mannopyranosylbromid, Isopropylalkohol;

DOI:10.1016/S0008-6215(00)81450-0

upstream raw materials:

2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide

N,N-dimethylformamide diisopropyl acetal

isopropyl alcohol

Downstream raw materials:

(3aS,5R,6S,7S,7aS)-2-Isopropoxy-2-methyl-5-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-6,7-diol