22331-21-1

Basic information

• Product Name: 3-O-Benzyl-1,2:5,6-bis-O-isopropylidene-alpha-D-galactofuranose
• Synonyms: 3-O-BENZYL-1,2:5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-ALLOFURANOSE;3-O-Benzyl-1,2:5,6-di-O-isopropylidene-a-D-allofuranose;3-O-Benzyl-1,2:5,6-bis-O-isopropylidene-alpha-D-galactofuranose;1,2 : 5,6-Di-O-isopropylidene-3-O- benzyl-α-D- rib;a-D-Allofuranose, 1,2:5,6-bis-O-(1-Methylethylidene)-3-O-(phenylMethyl)-;3-O-benzyl-1,2;3-O-Benzyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose;3-O-Benzyl-1,2:5,6-bis(di-O-isopropylidene)--D-allofuranose
• CAS NO: 22331-21-1
• Molecular Formula: C₁₉H₂₆O₆
• Molecular Weight: 350.41
• Mol File: 22331-21-1.mol
• Article Data: 24

Chemical Properties

• Melting Point: 65-66 °C
• Boiling Point: 422.6±45.0 °C(Predicted)
• Appearance: /
• Density: 1.21±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 3-O-Benzyl-1,2:5,6-bis-O-isopropylidene-alpha-D-galactofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-Benzyl-1,2:5,6-bis-O-isopropylidene-alpha-D-galactofuranose(22331-21-1)
• EPA Substance Registry System: 3-O-Benzyl-1,2:5,6-bis-O-isopropylidene-alpha-D-galactofuranose(22331-21-1)

Safety Data

• Hazardous Substances Data: 22331-21-1(Hazardous Substances Data)

Usage

General Description

3-O-Benzyl-1,2:5,6-bis-O-isopropylidene-alpha-D-galactofuranose is a chemical compound with a complex molecular structure. It is composed of a galactose sugar molecule that has been modified with benzyl and isopropyl groups. The compound has several functional groups, including an ether linkage and two acetal groups, which contribute to its stability and reactivity. 3-O-Benzyl-1,2:5,6-bis-O-isopropylidene-alpha-D-galactofuranose is commonly used in organic synthesis and chemical reactions as a building block for creating more complex molecules. Its unique structure and reactivity make it a valuable tool for researchers and chemists in various fields.

Upstream product

• 14686-89-6 (1,2:5,6)-di-O-isopropylidene-D-gulose 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 2595-05-3 Diacetone D-glucose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 4205-23-6 D-gulose 
• 50-99-7 D-glucose 
• 65434-49-3 3-O-benzyl-1,2-O-isopropylidene-α-D-galactofuranose 
• 77-76-9 2,2-dimethoxy-propane 
• 22331-19-7 3-O-benzyl-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose 
• 22529-61-9 (1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol 
• 35777-79-8 5,6-di-O-benzoyl-3-O-benzyl-1,2-O-isopropylidene-β-L-idofuranose 
• 286011-06-1 1,2:5,6-di-O-isopropylidene-α-D-galactofuranose 

Downstream Products

• 57099-04-4 3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose 
• 5531-09-9 3-O-benzyl-D-allopyranose 
• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 
• 184229-59-2 3-O-benzyl-1,2:5,6-tetra-O-acetyl-β-D-allofuranose 
• 182698-06-2 C₄₁H₃₄O₁₀ 
• 65877-63-6 3-O-benzyl-D-glucopyranose 
• 124468-96-8 1,2-Isopropylidene-3-O-benzyl-6-O-benzoyl-α-D-allofuranose 
• 230631-30-8 6-O-Benzoyl-3,5-di-O-benzyl-1,2-di-O-isopropylidene-α-D-allofuranose 
• 230631-31-9 1,2-Di-O-acetyl-6-O-benzoyl-3,5-di-O-benzyl-D-allofuranose 
• 663174-82-1 1-((1S,4R,5R,7R,8R)-4,8-Bis-benzyloxy-2,6-dioxa-bicyclo[3.2.1]oct-7-yl)-1H-[1,3,5]triazine-2,4-dione 
• 663174-83-2 4-Amino-1-((1S,4R,5R,7R,8R)-4,8-bis-benzyloxy-2,6-dioxa-bicyclo[3.2.1]oct-7-yl)-1H-[1,3,5]triazin-2-one 
• 663174-81-0 1-[(2R,3R,4S,5R)-4-Benzyloxy-5-((R)-1-benzyloxy-2-hydroxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-1H-[1,3,5]triazine-2,4-dione 
• 63593-02-2 3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose 
• 63593-03-3 1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose 

Relevant articles and documents

6-Methylpurine derived sugar modified nucleosides: Synthesis and evaluation of their substrate activity with purine nucleoside phosphorylases

6-Methylpurine (MeP) is cytotoxic adenine analog that does not exhibit selectivity when administered systemically, and could be very useful in a gene therapy approach to cancer treatment involving Escherichia coli PNP. The prototype MeP releasing prodrug, 9-(β-d-ribofuranosyl)-6-methylpurine, MeP-dR has demonstrated good activity against tumors expressing E. coli PNP, but its antitumor activity is limited due to toxicity resulting from the generation of MeP from gut bacteria. Therefore, we have embarked on a medicinal chemistry program to identify non-toxic MeP prodrugs that could be used in conjunction with E. coli PNP. In this work, we report on the synthesis of 9-(6-deoxy-β-d-allofuranosyl)-6-methylpurine (3) and 9-(6-deoxy-5-C-methyl-β-d-ribo-hexofuranosyl)-6-methylpurine (4), and the evaluation of their substrate activity with several phosphorylases. The glycosyl donors; 1,2-di-O-acetyl-3,5-di-O-benzyl-α-d-allofuranose (10) and 1-O-acetyl-3-O-benzyl-2,5-di-O-benzoyl-6-deoxy-5-C-methyl-β-d-ribohexofuran-ose (15) were prepared from 1,2:5,6-di-O-isopropylidine-α-d-glucofuranose in 9 and 11 steps, respectively. Coupling of 10 and 15 with silylated 6-methylpurine under Vorbrüggen glycosylation conditions followed conventional deprotection of the hydroxyl groups furnished 5'-C-methylated-6-methylpurine nucleosides 3 and 4, respectively. Unlike 9-(6-deoxy-α-l-talo-furanosyl)-6-methylpurine, which showed good substrate activity with E. coli PNP mutant (M64V), the β-d-allo-furanosyl derivative 3 and the 5'-di-C-methyl derivative 4 were poor substrates for all tested glycosidic bond cleavage enzymes.

NOVEL PROCESS FOR MAKING ALLOFURANOSE FROM GLUCOFURANOSE

The present invention relates to the manufacture of allofuranose from glucofuranose as defined in the description and in the claim. Allofuranos is an intermediate in the manufacture of oligonucleotides which can be used as a medicament.

Anaerobic 5-Hydroxybenzimidazole Formation from Aminoimidazole Ribotide: An Unanticipated Intersection of Thiamin and Vitamin B12 Biosynthesis

Comparative genomics of the bacterial thiamin pyrimidine synthase (thiC) revealed a paralogue of thiC (bzaF) clustered with anaerobic vitamin B12 biosynthetic genes. Here we demonstrate that BzaF is a radical S-adenosylmethionine enzyme that catalyzes the remarkable conversion of aminoimidazole ribotide (AIR) to 5-hydroxybenzimidazole (5-HBI). We identify the origin of key product atoms and propose a reaction mechanism. These studies represent the first step in solving a long-standing problem in anaerobic vitamin B12 assembly and reveal an unanticipated intersection of thiamin and vitamin B12 biosynthesis.