75499-83-1

Basic information

• Product Name: D-Glucitol,2,5-anhydro-,4,6-dibenzoate
• Synonyms: D-Glucitol,2,5-anhydro-,4,6-dibenzoate;2,5-Anhydro-4,6-di-O-benzoyl-D-glucitol
• CAS NO: 75499-83-1
• Molecular Formula: C₂₀H₂₀O₇
• Molecular Weight: 372.371
• Product Categories: Sugars
• Mol File: 75499-83-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: D-Glucitol,2,5-anhydro-,4,6-dibenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: D-Glucitol,2,5-anhydro-,4,6-dibenzoate(75499-83-1)
• EPA Substance Registry System: D-Glucitol,2,5-anhydro-,4,6-dibenzoate(75499-83-1)

Safety Data

• Hazardous Substances Data: 75499-83-1(Hazardous Substances Data)

Upstream product

• 75499-82-0 2,5-anhydro-4,5-di-O-benzoyl-1,3-O-isopropylidene-D-glucitol 
• 198775-13-2 ((3R,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-methanol 
• 37699-02-8 (3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-carbaldehyde 
• 98-88-4 benzoyl chloride 
• 65729-81-9 2,5-anhydro-1,3-O-isopropylidene-D-glucitol 
• 69-65-8 mannitol 
• 67-64-1 acetone 
• 27826-73-9 2,5-anhydro-D-glucitol 

Downstream Products

• 77909-73-0 C₂₁H₁₈O₇S 
• 243469-59-2 2,5-anhydro-1-azido-1-deoxy-D-glucitol 
• 243132-01-6 2,5-anhydro-1-azido-4,5-di-O-benzoyl-1-deoxy-D-glucitol 
• 64915-00-0 β-2'-deoxyshowdomycin 
• 2303-35-7 (+)-muscarine chloride 
• 77890-05-2 C₂₃H₁₉NO₇ 
• 82462-49-5 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexonic acid 
• 198775-27-8 3-Benzoyl-5-methyl-1-((2R,5S)-5-trityloxymethyl-2,5-dihydro-furan-2-ylmethyl)-1H-pyrimidine-2,4-dione 
• 198775-36-9 2,5-anhydro-4,6-di-O-benzoyl-1-(N-3-benzoylthymin-1-yl)-3-deoxy-D-ribo-hexitol 
• 198775-21-2 2,5-anhydro-1-O-t-butyldimethylsilyl-6-O-triphenylmethyl-D-glucitol 
• 198775-23-4 2,5-anhydro-1-O-t-butyldimethylsilyl-6-O-triphenylmethyl-D-erythro-hex-3,4-enitol 
• 198775-25-6 ((2R,5S)-5-Trityloxymethyl-2,5-dihydro-furan-2-yl)-methanol 
• 198775-19-8 2,5-anhydro-4,6-di-O-benzoyl-1-O-t-butyldimethylsilyl-D-glucitol 
• 77890-04-1 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol 

Relevant articles and documents

D-arbinose-based synthesis of homo-C-d4T and homo-C-thymidine

2,3,5-Tri-O-benzyl-D-arabinofuranosyl halides (chloride, bromide) were reacted with AllMgBr, MeMgBr, and VinMgBr to furnish anomeric mixtures of the C-glycosyl products. The factors that influenced the β/α ratio are discussed. The α,β-C-vinyl derivative was transformed into 1-deoxy-1-C-hydroxymethyl-β and α-D-arabinofuranoses (2,5-anhydro-D-glucitol and -mannitol, respectively), separable after isopropylidenation step. 2,5-Anhydro-1,3-O-isopropylidene-D-glucitol was converted into 2,5-anhydro-6-O-triphenylmethyl-D-erythro-hex-3,4-enitol and 2,5-anhydro-4,6-di-O-benzoyl-3-deoxy-D-ribo-hexitol, which were coupled with N-3-benzoylthymine under the Mitsunobu conditions to furnish two analogs of nucleosides with a -CH2- insert between sugar moieties and thymine. (Chemical Equation Presented).

Synthesis of homo-C-D4T and homo-C-thymidine

β-C-Vinyl glycoside of D-arabinofuranose was converted to the β-C- hydroxymethyl glycoside 12 which was condensed with N-3-benzoyl thymine under Mitsunobu conditions to furnish homo-C-analog 14 of the 2',3'-dideoxy-2',3'- didehydrothymidine (D4T). Synthesis of the homo-C-thymidine 18 was accomplished by the same procedure from compound 15.