132047-01-9

Basic information

• Product Name: 5-O-(Trimethylsilyl)-6,7:8,9:10,11-tri-O-isopropylidene-2,3-dideoxy-D-arabino-L-altro-undec-2-enono-1,4-lactone
• Synonyms: 5-O-(Trimethylsilyl)-6,7:8,9:10,11-tri-O-isopropylidene-2,3-dideoxy-D-arabino-L-altro-undec-2-enono-1,4-lactone
• CAS NO: 132047-01-9
• Molecular Weight: 486.635
• Mol File: 132047-01-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 5-O-(Trimethylsilyl)-6,7:8,9:10,11-tri-O-isopropylidene-2,3-dideoxy-D-arabino-L-altro-undec-2-enono-1,4-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-O-(Trimethylsilyl)-6,7:8,9:10,11-tri-O-isopropylidene-2,3-dideoxy-D-arabino-L-altro-undec-2-enono-1,4-lactone(132047-01-9)
• EPA Substance Registry System: 5-O-(Trimethylsilyl)-6,7:8,9:10,11-tri-O-isopropylidene-2,3-dideoxy-D-arabino-L-altro-undec-2-enono-1,4-lactone(132047-01-9)

Safety Data

• Hazardous Substances Data: 132047-01-9(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 61550-02-5 (furan-2-yloxy)-trimethylsilane 
• 132077-98-6 2,3:4,5:6,7-Tri-O-isopropylidene-D-glycero-D-talo-heptose 

Relevant articles and documents

Ascent of the Aldose Series by Four Carbon Atoms: Total Synthesis of D-glycero-D-talo-L-talo-Undecose Pentaacetonide

Enantiomerically pure undecose acetonide 9 was synthesized, through heptose intermediate 5, starting with D-glyceraldehyde acetonide (1).The key steps were two consecutive four-carbon homologations, each consisting of four reactions: (i) stereoselective elongation of the aldehyde precursor with 2-(trimethylsiloxy)furan, giving Cn+4 butenolide templates 2 and 6, (ii) anti-selective cis-dihydroxylation of the butenolide double bond, giving fully functionalized lactones 3 and 7, (iii) lactone ring opening and protection, giving open-chain methyl esters 4 and 8, and (iv) DIBAL reduction to aldoses 5 and 9.At the end of the eight-step sequence, undecose 9 was prepared in a 5.1percent overall yield, which corresponded to a 69.5percent average yield per step.