beta-L-glucose pentaacetate

Base Information

• Chemical Name: beta-L-glucose pentaacetate
• CAS No.: 66966-07-2
• Molecular Formula: C16H22O11
• Molecular Weight: 390.344
• Mol file: 66966-07-2.mol

Synonyms:beta-L-glucose pentaacetate;1,2,3,4,6-Penta-O-acetyl-β-L-glucopyranose;β-L-Glucose Pentaacetate

Chemical Property of beta-L-glucose pentaacetate

Chemical Property:

• PSA: 140.73000
• LogP: -0.36740
• Storage Temp.: Refrigerator

Purity/Quality:

97% ^*data from raw suppliers

β-L-Glucose Pentaacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Displays insulinotropic potential.

Technology Process of beta-L-glucose pentaacetate

There total 52 articles about beta-L-glucose pentaacetate 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: 59.0%

1,3,4,6-tetra-O-acetyl-2-O-trityl-α-D-galactopyranose (130052-61-8) + 3,4,6-tri-O-acetyl-2-O-benzyl-β-D-galactopyranosyl thiocyanate (130052-60-7) → 1,3,4,6-tetra-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranose (130052-63-0) + Acetic acid (2R,3S,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-isothiocyanato-tetrahydro-pyran-4-yl ester (130052-67-4) + penta-O-acetyl-α-D-galactopyranose (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5)

Guidance literature:

With triphenylmethyl perchlorate; In dichloromethane; Ambient temperature;

DOI:10.1016/0008-6215(91)84047-I

Reference yield: 56.0%

chloramphenicol (56-75-7,85666-84-8) + β-D-galactose peracetate (4163-60-4) → O1-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)chloramphenicol + penta-O-acetyl-α-D-galactopyranose (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; for 0.25h;

DOI:10.1081/CAR-120013493

Reference yield: 52.0%

1,3,4,6-tetra-O-acetyl-2-O-trityl-α-D-galactopyranose (130052-61-8) + 3,4-di-O-acetyl-2-O-benzyl-α-L-arabinopyranosyl thiocyanate (135593-74-7) → 1,3,4,6-tetra-O-acetyl-2-O-(2,4-di-O-acetyl-2-O-benzyl-β-L-arabinopyranosyl)-α-D-galactopyranose (135617-25-3) + 3,4-di-O-acetyl-2-O-benzyl-β-L-arabinopyranosyl isothiocyanate + penta-O-acetyl-α-D-galactopyranose (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5)

Guidance literature:

With triphenylmethyl perchlorate; In dichloromethane; at -5 ℃; for 5.5h;

DOI:10.1016/0008-6215(91)84047-I

upstream raw materials:

β-D-mannose

acetic anhydride

D-Mannose

D-Mannose

Downstream raw materials:

1-O-p-nitrophenyl-2,3,4,6-tetra-O-acetyl α-D-mannopyranoside

ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-mannopyranoside

S-ethyl 2,3,4,6-tetra-O-acetyl-1-deoxy-1-thio-α-D-mannopyranoside

1-O-phenyl-2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside