β-L-Arabinopyranose tetraacetate

Base Information

• Chemical Name: β-L-Arabinopyranose tetraacetate
• CAS No.: 4258-00-8
• Molecular Formula: C13H18O9
• Molecular Weight: 318.281
• Mol file: 4258-00-8.mol

Synonyms:β-L-Arabinopyranose, 1,2,3,4-tetraacetate;(2R,3R,4S,5S)-tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

Chemical Property of β-L-Arabinopyranose tetraacetate

Chemical Property:

• PSA: 114.43000
• LogP: -0.29910

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of β-L-Arabinopyranose tetraacetate

There total 60 articles about β-L-Arabinopyranose tetraacetate 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: 100.0%

L-(+)-arabinose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) + acetic anhydride (108-24-7) → 1,2,3,4-tetra-O-acetyl-L-arabinopyranose (1233-03-0,2595-11-1,4026-34-0,4049-33-6,4049-34-7,4257-95-8,4257-98-1,4258-00-8,4627-30-9,17080-99-8,19186-37-9,25227-11-6,25243-38-3,62446-93-9,62929-49-1,67226-03-3,78087-60-2,78088-17-2,82890-16-2,86782-34-5,86782-35-6,92218-63-8,99880-95-2,108646-05-5,115939-79-2,142130-89-0,123163-97-3)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/j.bmc.2003.12.034

Reference yield: 100.0%

D-xylose (6763-34-4) + acetic anhydride (108-24-7) → α-D-xylopyranose tetraacetate (1233-03-0,2595-11-1,4026-34-0,4049-33-6,4049-34-7,4257-95-8,4257-98-1,4258-00-8,4627-30-9,17080-99-8,19186-37-9,25227-11-6,25243-38-3,62446-93-9,62929-49-1,67226-03-3,78087-60-2,78088-17-2,82890-16-2,86782-34-5,86782-35-6,92218-63-8,99880-95-2,108646-05-5,115939-79-2,123163-97-3,142130-89-0)

Guidance literature:

D-xylose; With dmap; triethylamine; In dichloromethane; at 0 - 25 ℃; for 0.166667h; Inert atmosphere;

acetic anhydride; In dichloromethane; at 0 - 25 ℃; for 1h; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.carres.2017.03.008

Reference yield: 94.0%

D-Xylose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2) + acetic anhydride (108-24-7) → α-D-xylopyranose tetraacetate (1233-03-0,2595-11-1,4026-34-0,4049-33-6,4049-34-7,4257-95-8,4257-98-1,4258-00-8,4627-30-9,17080-99-8,19186-37-9,25227-11-6,25243-38-3,62446-93-9,62929-49-1,67226-03-3,78087-60-2,78088-17-2,82890-16-2,86782-34-5,86782-35-6,92218-63-8,99880-95-2,108646-05-5,115939-79-2,123163-97-3,142130-89-0)

Guidance literature:

With dmap; In pyridine; Inert atmosphere;

DOI:10.1016/j.tet.2014.07.052

upstream raw materials:

L-(+)-arabinose

acetic anhydride

L-arabinose

acetyl chloride

Downstream raw materials:

1,2,3,4-tetra-O-acetyl-α-L-arabinopyranose

tetra-O-acetyl-β-D-xylopyranose

(4-nitro-phenyl)-(tri-O-acetyl-β-L-arabinopyranoside)

(4-nitro-phenyl)-(tri-O-acetyl-α-L-arabinopyranoside)

Refernces

• 1、 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.
• 2、 Liang, Yang,Pedersen, Christian M.. "Protecting carbohydrates with ethers, acetals and orthoesters under basic conditions". supporting information. p. 7598 - 7601. Retrieved 2021/09/22.