3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose

Base Information

• Chemical Name: 3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose
• CAS No.: 160882-25-7
• Molecular Formula: C₁₂H₁₆O₃S
• Molecular Weight: 240.323
• Mol file: 160882-25-7.mol

Synonyms:3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose

Chemical Property of 3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose

Chemical Property:

Purity/Quality:

min 99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose

There total 11 articles about 3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose 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: 90.0%

→ 3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose (160882-25-7)

Guidance literature:

Reference yield: 71.0%

methyl 2,5-anhydro-3-O-benzyl-2,5-dideoxy-2-thio-β-D-arabino-pentofuranoside (160882-24-6) → 3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose (160882-25-7)

Guidance literature:

With sodium cyanoborohydride; acetic acid; In water; at 40 ℃;

DOI:10.1016/0040-4039(94)88293-2

Reference yield:

2,5-dideoxy-2,5-epithio-3-O-benzyl-D-lyxofuranoside (347362-38-3) → 3-O-benzyl-1-deoxy-4-thio-D-arabino-furanose (160882-25-7)

Guidance literature:

With hydrogenchloride; sodium tetrahydroborate; Yield given. Multistep reaction; 1) THF; 2) MeOH;

DOI:10.1021/jo9519423

upstream raw materials:

methyl 2,5-anhydro-3-O-benzyl-2,5-dideoxy-2-thio-β-D-arabino-pentofuranoside

2,5-dideoxy-2,5-epithio-3-O-benzyl-D-lyxofuranoside

methyl 3-O-benzyl-2,5-di-O-methanesulfonyl-D-furanoyl glucoside

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

Benzoic acid (2R,3S,4R,5R)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-4-azido-2-hydroxymethyl-tetrahydro-thiophen-3-yl ester

Benzoic acid (2R,3S,4R,5S)-5-(4-acetylamino-2-oxo-2H-pyrimidin-1-yl)-4-azido-2-hydroxymethyl-tetrahydro-thiophen-3-yl ester

Refernces

• 1、 Muraoka, Osamu,Yoshikai, Kazuya,Takahashi, Hideo,Minematsu, Toshie,Lu, Guangxin,Tanabe, Genzoh,Wang, Tao,Matsuda, Hisashi,Yoshikawa, Masayuki. "Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity". . p. 500 - 509. Retrieved 2007/10/03.
• 2、 -. "Purine 4'-thioarabinonucleosides". . . Retrieved 2008/06/13.