109922-65-8

Basic information

• Product Name: C₄₇H₅₈O₁₇
• CAS NO: 109922-65-8
• Molecular Weight: 894.967
• Mol File: 109922-65-8.mol

Chemical Properties

• CAS DataBase Reference: C₄₇H₅₈O₁₇(CAS DataBase Reference)
• NIST Chemistry Reference: C₄₇H₅₈O₁₇(109922-65-8)
• EPA Substance Registry System: C₄₇H₅₈O₁₇(109922-65-8)

Safety Data

• Hazardous Substances Data: 109922-65-8(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 109922-66-9 C₄₁H₅₂O₁₄ 
• 106711-67-5 C₁₅H₁₉ClO₅ 
• 106711-60-8 Acetic acid (2R,3R,4S,5R,6S)-4-benzyloxy-5-((2S,3R,4S,5R,6R)-3,5-diacetoxy-4-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-hydroxy-2-methyl-tetrahydro-pyran-3-yl ester 
• 82167-83-7 C₁₅H₂₀O₆ 
• 106711-60-8 Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-2-((2S,3R,4S,5R,6R)-5-acetoxy-4-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-3-yloxy)-4-benzyloxy-6-methyl-tetrahydro-pyran-3-yl ester 
• 109922-62-5 C₂₆H₃₄O₉ 
• 106711-53-9 C₁₈H₂₄O₅ 
• 106711-50-6 3-O-Benzyl-6-deoxy-D-glucose 
• 18439-45-7 3-O-Benzyl-6-desoxy-1,2-O-isopropyliden-α-D-gluco-hexofuranose 
• 106711-57-3 Acetic acid (2R,3R,4S,5R,6S)-6-allyloxy-4-benzyloxy-5-((2S,3R,4S,5R,6R)-3,5-diacetoxy-4-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester 
• 106711-58-4 Acetic acid (2R,3R,4S,5R,6R)-6-allyloxy-4-benzyloxy-5-((2S,3R,4S,5R,6R)-3,5-diacetoxy-4-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-2-methyl-tetrahydro-pyran-3-yl ester 
• 106711-54-0 C₂₀H₂₆O₆ 
• 106711-51-7 acetyl 2,4-O-diacetyl-3-O-benzyl-6-deoxy-α/β-D-glucopyranoside 

Relevant articles and documents

Phyllanthoside-Phyllanthostatin Synthetic Studies. 8. Total Synthesis of (+)-Phyllanthoside. Development of the Mitsunobu Glycosyl Ester Protocol

The first total syntheses of the antineoplastic glycoside (+)-phyllanthoside (1) and the parent disaccharide (-)-phyllanthose (5) have been achieved. Stereoselective Koenigs-Knorr coupling of two 6-deoxyglucose derivatives, bromide 54 and alcohol 55, generated the uncommon 1′ → 2β glycosidic linkage of (-)-phyllanthose. A stereochemically convergent Mitsunobu reaction of protected disaccharide 87 with aglycon carboxylic acid 80, prepared via asymmetric synthesis, then led to 1 of high enantiomeric purity. The Mitsunobu procedure comprises an efficient general method for stereospecific assembly of β-glycosyl esters.

AN EFFICIENT SYNTHESIS OF GLYCOSYL ESTERS EXPLOITING THE MITSUNOBU REACTION.

The anomeric hydroxyl group of various pyranose hemiacetals can be esterified with inversion of configuration, conveniently, mildly and on large-scale using triphenylphosphine (TPP), with either diisopropylazodicarboxylate (DIAD) or diethylazodicarboxylat