127214-37-3

Basic information

• Product Name: (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran
• Synonyms: (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran
• CAS NO: 127214-37-3
• Molecular Weight: 460.57
• Mol File: 127214-37-3.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran(127214-37-3)
• EPA Substance Registry System: (2S,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-methoxy-6-vinyl-tetrahydro-pyran(127214-37-3)

Safety Data

• Hazardous Substances Data: 127214-37-3(Hazardous Substances Data)

Upstream product

• 1031-15-8 methyltriphenylphosphonium chloride 
• 83051-88-1 methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 2065-66-9 methyl-triphenylphosphonium iodide 
• 79-37-8 oxalyl dichloride 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 210834-15-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 3879-79-6 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 27200-84-6 methyl triphenylphosphonium bromide 
• 19493-09-5 Methylenetriphenylphosphorane 

Downstream Products

• 103597-20-2 methyl 2,3,4-tri-O-benzyl-D-glycero-α-D-gluco-heptopyranoside 
• 133918-92-0 METHYL 2,3,4-TRI-O-BENZYL-6-DEOXY-α-D-GLUCOHEPTOPYRANOSIDE 
• 1207950-87-5 C₅₆H₆₀O₁₀ 
• 188011-82-7 1-((2S,3S,4S,5R,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)ethanone 
• 1400906-97-9 methyl 2,3,4-tri-O-benzyl-α-D-glucoheptopyranoside-7-isobutyrate 
• 1400906-87-7 1-methyl-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucoheptopyranuronic acid 
• 1400907-03-0 1,8-dimethyl-2,3,4-tri-O-benzyl-β-D-glucooctopyrano-7-ulose 
• 1400906-84-4 1-methyl-2,3,4-tri-O-benzyl-8-deoxy-8-diazo-α-D-glucoheptopyran-7-ulose 
• 1400907-00-7 1-methyl-2,3,4-tri-O-benzyl-β-D-glucoheptopyrano-2(Z)-butene-6,6'-dione 
• 1400907-01-8 1-methyl-2,3,4-tri-O-benzyl-β-D-glucoheptopyrano-2(E)-butene-6,6'-dione 
• 1350433-86-1 (4S,5R,6S)-4,5,6-tris(acetoxy)-2-methylcyclohex-2-enone 
• 1187828-02-9 (2S,3R,4S,6R)-2,3,4-trihydroxy-6-methylcyclohexanone 
• 1187828-00-7 (4S,5R,6S)-4,5,6-tris(benzyloxy)-2-methylcyclohex-2-enone 

Relevant articles and documents

Study on metal-induced reactions of α-diazocarbonyl glucosides

Conversions of diazocarbonyl carbohydrate compounds catalyzed by a series of rhodium and copper catalysts in conventional heating or microwave conditions were investigated. C-H insertion product was obtained in the presence of Rh 2(OAc)4. Intermolecular reactions rather than intramolecular reactions occurred in the presence of copper catalysts.

Synthesis of (6,6′)-C-linked pseudodisaccharides

A series of (6,6′)-C-linked pseudodisaccharides has been prepared using a general synthetic strategy of olefin metathesis in the presence of Grubbs second-generation catalyst. Yields were excellent in every case.

Synthesis of vinyl- and alkynylcyclopentanetetraols by SmI2/Pd(0)-promoted carbohydrate ring-contraction

A variety of vinyl- or alkynyl-substituted polyhydroxylated cyclopentanes and cyclobutanes are prepared in enantiomerically pure form from appropriate carbohydrate precursors, in a direct one-step ring-contraction procedure promoted by SmI2 and catalytic Pd(0). This reaction is thought to proceed through intermediate ring-opened allyl- or allenylsamarium complexes that undergo ring-closure by intramolecular carbonyl addition. A predominant trans relationship is found between vinyl (or alkynyl) and hydroxyl groups at the two newly created stereogenic centers, with good to excellent levels of stereoselectivity being observed in the formation of homopropargyl cyclopentanol products. Under appropriate conditions, preparatively useful yields are realized of stereoisomers not directly available using alternative methodology.