1,2,3,4-TETRA-O-ACETYL-ALPHA-D-ARABINOPYRANOSE

Base Information

• Chemical Name: 1,2,3,4-TETRA-O-ACETYL-ALPHA-D-ARABINOPYRANOSE
• CAS No.: 108646-05-5
• Molecular Formula: C13H18 O9
• Molecular Weight: 318.281
• Hs Code.: 2932999099
• Mol file: 108646-05-5.mol

Synonyms:Peracetyl-D-arabinose

Chemical Property of 1,2,3,4-TETRA-O-ACETYL-ALPHA-D-ARABINOPYRANOSE

Chemical Property:

• Boiling Point: 362.9±42.0 °C(Predicted)
• PSA: 114.43000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: -0.29910

Purity/Quality:

98% ^*data from raw suppliers

1,2,3,4-Tetra-O-acetyl-a-D-arabinopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2,3,4-TETRA-O-ACETYL-ALPHA-D-ARABINOPYRANOSE

There total 56 articles about 1,2,3,4-TETRA-O-ACETYL-ALPHA-D-ARABINOPYRANOSE 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:

D-xylose

acetic anhydride

tetra-O-acetyl-β-D-xylopyranose

D-Xylose

Downstream raw materials:

tetra-O-acetyl-β-D-xylopyranose

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

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

2-methylphenyl-α-L-arabinopyranoside

Refernces

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• 5、 Mukhopadhyay, Balaram,Kartha, K.P. Ravindranathan,Russell, David A.,Field, Robert A.. "Streamlined synthesis of per-O-acetylated sugars, glycosyl iodides, or thioglycosides from unprotected reducing sugars". . p. 7758 - 7760. Retrieved 2004.
• 6、 Alcaro,Arena,Neri,Ottana,Ortuso,Pavone,Vigorita. "Design and synthesis of DNA-intercalating 9-fluoren-β-O-glycosides as potential IFN-inducers, and antiviral and cytostatic agents". . p. 1781 - 1791. Retrieved 2004.
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• 9、 Borowiecka, Joanna,Michalska, Maria. "Novel stereoselective synthesis of glycosyl-1-O-acyl esters via peracetylglycosyl phosphorothioates, -selenoates and -dithioates as glycosyl donors". . p. 858 - 862. Retrieved 1996.
• 10、 Ichikawa, Shuji,Tomita, Isao,Hosaka, Akira,Sato, Tadashi. "Metal-Catalyzed Organic Photoreactions. Iron (III)-Catalyzed Photoreactions of Aldo- and Ketohexoses". . p. 513 - 520. Retrieved 1988.