D-Galactopyranose pentaacetate

Base Information

• Chemical Name: D-Galactopyranose pentaacetate
• CAS No.: 25878-60-8
• Molecular Formula: C16H22O11
• Molecular Weight: 390.344
• Hs Code.: 2932999099
• Mol file: 25878-60-8.mol

Synonyms:D-Galactopyranose,pentaacetate (9CI);Galactopyranose, pentaacetate, D- (8CI);1,2,3,4,6-Penta-O-acetyl-D-galactopyranose;1,2,3,4,6-penta-O-acetylgalactopyranose;1,2,3,4,6-Penta-O-acetyl-D-galactopyranoside;

Chemical Property of D-Galactopyranose pentaacetate

Chemical Property:

• Vapor Pressure: 9.23E-08mmHg at 25°C
• Melting Point: 113°C
• Refractive Index: 1.482
• Boiling Point: 434.8 °C at 760 mmHg
• Flash Point: 188.1 °C
• PSA: 140.73000
• Density: 1.3 g/cm³
• LogP: -0.36740
• Storage Temp.: 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

1,2,3,4,6-Penta-O-acetyl-D-galactopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,N
• Hazard Codes: T,N

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,2,3,4,6-Penta-O-acetyl-D-galactopyranose is used for production of fucosylated carbohydrates by enzymic fucosylation synthesis of sugar nucleotides.

Technology Process of D-Galactopyranose pentaacetate

There total 59 articles about D-Galactopyranose 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

Refernces

• 1、 Ahmed, Ajaz,Bhagat, Kavita,Choudhary, Sushil,Kaur Gulati, Harmandeep,Kumar, Ajay,Kumar, Nitish,Mukherjee, Debaraj,Singh Bedi, Preet Mohinder,Singh, Atamjit,Singh, Harbinder,Vir Singh, Jatinder. "Design, Synthesis, biological investigations and molecular interactions of triazole linked tacrine glycoconjugates as Acetylcholinesterase inhibitors with reduced hepatotoxicity". . . Retrieved 2021/11/23.
• 2、 Li, Xiao-San,Chen, Tang-Ji,Xu, Zhi-Peng,Long, Juan,He, Miao-Ying,Zhan, He-Hui,Zhuang, Hai-Cai,Wang, Qi-Lin,Liu, Li,Yang, Xue-Mei,Tang, Jin-Shan. "Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents". . . Retrieved 2021/12/30.