100906-48-7

Basic information

• Product Name: (E,S,S)-methyl 4-O-benzyl-5,6-di-O-isopropylidene-4,5,6-trihydroxy-2-hexenoate
• Synonyms: (E,S,S)-methyl 4-O-benzyl-5,6-di-O-isopropylidene-4,5,6-trihydroxy-2-hexenoate
• CAS NO: 100906-48-7
• Molecular Weight: 306.359
• Mol File: 100906-48-7.mol

Chemical Properties

• CAS DataBase Reference: (E,S,S)-methyl 4-O-benzyl-5,6-di-O-isopropylidene-4,5,6-trihydroxy-2-hexenoate(CAS DataBase Reference)
• NIST Chemistry Reference: (E,S,S)-methyl 4-O-benzyl-5,6-di-O-isopropylidene-4,5,6-trihydroxy-2-hexenoate(100906-48-7)
• EPA Substance Registry System: (E,S,S)-methyl 4-O-benzyl-5,6-di-O-isopropylidene-4,5,6-trihydroxy-2-hexenoate(100906-48-7)

Safety Data

• Hazardous Substances Data: 100906-48-7(Hazardous Substances Data)

Upstream product

• 100906-42-1 2-O-benzyl-3,4-O-isopropylidene-L-threose 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 88738-78-7 bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate 
• 100-39-0 benzyl bromide 
• 84379-53-3 2-O-benzyl-3,4-O-isopropylidene-L-threitol 
• 114185-07-8 ethyl (2R)-2-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-2-hydroxyacetate 
• 340699-28-7 ethyl (2R,3S)-2-O-benzyl-3,4-O-isopropylidene-2,3,4-trihydroxybutanoate 
• 38270-72-3 dimethyl 2,3-O-benzylidene-L-tartrate 
• 100-52-7 benzaldehyde 
• 100906-45-4 (5S,6S)-6-(benzyloxy)-2,2-dimethyl-1,3-dioxepan-5-ol 
• 866771-99-5 [(4'R,5'R)-5'-(benzyloxy)-2',2'-dimethyl-1',3'-dioxan-4'-yl]methanol 
• 84379-51-1 2-O-benzyl-L-threitol 

Relevant articles and documents

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A novel versatile method for the synthesis of all eight diastereomerically pure L-hexoses was developed. L-Ascorbic acid was converted to two diastereomers A. These α-hydroxy esters were transformed into four γ-alkoxy- α,β-unsaturated esters C via the int

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The syntheses of the chiral α,β-unsaturated lactones (+)-5, (-)-6, (+)-8, (+)-9, and (+)-10 have been efficiently achieved from readily available starting materials. The lactone (+)-5 has been synthesized in 7 steps from (R,R)-dimethyl tartrate (38-43% overall yield). The use of (+)-5 in formal syntheses of natural (+)-asperlin 4 and advanced intermediates for (+)-olguine 2 are also reported. The lactone (-)-6 has been prepared in 5 steps from (R)-malic and (44-50% overall yield). It can be a useful precursor for the syntheses of branched chain and deoxy nucleoside analogues. The preparation of (-)-6 constitutes formal syntheses of natural (+)-eldanolide 53 and the (+)-Geissman-Waiss lactone 54 (an intermediate for the syntheses of a variety of pyrrolizidine alkaloids). The lactones (+)-8, (+)-9 and (+)-10 have been synthesized from 3,4-di-O-acetyl-L-rhamnal 58. The highly diastereoselective transformations of (+)-9 and (+)-10, through sequential conjugate nucleophilic addition and enolate reaction, into densely functionalized chiral γ-lactones 12 are also reported. Copyright (C) Elsevier Science Ltd.

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