106929-09-3

Basic information

• Product Name: (2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal
• Synonyms: (2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal
• CAS NO: 106929-09-3
• Molecular Weight: 370.445
• Mol File: 106929-09-3.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal(106929-09-3)
• EPA Substance Registry System: (2S,3R,4R)-2,3-dibenzyloxy-4,5-isopropylidenedioxypentanal(106929-09-3)

Safety Data

• Hazardous Substances Data: 106929-09-3(Hazardous Substances Data)

Upstream product

• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 142760-40-5 2-[(1S,2R)-1,2-Bis-benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl]-thiazole 
• 142705-76-8 (R)-2-Benzyloxy-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-thiazol-2-yl-ethanone 
• 103795-14-8 (1R)-2-O-benzyl-3,4-O-isopropylidene-1-(2-thiazolyl)-D-erythritol 
• 142760-39-2 (1S,2R,3R)-2-O-benzyl-3,4-O-isopropylidene-1-(2-thiazolyl)-1,2,3,4-butanetetraol 
• 103795-10-4 (2R,3R)-1,2-O-Isopropylidene-3-(2-thiazolyl)-1,2,3-propanetriol 
• 118377-11-0 2-[(R)-Benzyloxy-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methyl]-3-methyl-thiazol-3-ium; iodide 
• 103795-11-5 (1R)-1-O-benzyl-2,3-O-isopropylidene-1-(2-thiazolyl)-D-glycitol 
• 103795-12-6 (R)-2-(benzyloxy)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde 
• 100-39-0 benzyl bromide 
• 1941-50-0 D-arabinose diethyl dithioacetal 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 69-65-8 mannitol 
• 111476-62-1 3,4-di-O-benzyl-1,2:5,6-di-O-isopropylidene-D-mannitol 

Downstream Products

• 445396-57-6 (R)-4-((1S,2R)-1,2-Bis-benzyloxy-propyl)-2,2-dimethyl-[1,3]dioxolane 
• 436148-63-9 1-deoxy-1-iodo-2,3-di-O-benzyl-4,5-O-isopropylidene-D-arabinitol 
• 436148-71-9 (3R,4S)-3,4-Bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-phenyl-butan-1-one 
• 436148-73-1 (3R,4S)-3,4-Bis-benzyloxy-1-(3-chloro-phenyl)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-1-one 
• 436148-72-0 (3R,4S)-3,4-Bis-benzyloxy-1-(4-chloro-phenyl)-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-1-one 
• 436148-74-2 (3R,4S)-3,4-Bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-p-tolyl-butan-1-one 
• 436148-75-3 (3R,4S)-3,4-Bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-(4-fluoro-phenyl)-butan-1-one 
• 436148-76-4 (3R,4S)-1-Benzo[1,3]dioxol-5-yl-3,4-bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-butan-1-one 
• 436148-77-5 (3R,4S)-3,4-Bis-benzyloxy-4-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-(3,4,5-trimethoxy-phenyl)-butan-1-one 
• 436148-64-0 (4R,5S)-4,5-Bis-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-morpholin-4-yl-2-phenyl-pentanenitrile 
• 436148-67-3 (4R,5S)-4,5-Bis-benzyloxy-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-morpholin-4-yl-2-p-tolyl-pentanenitrile 

Relevant articles and documents

Palladium(II)-catalyzed cyclization of urethanes and its application to a total synthesis of 1-deoxynojirimycin

We have employed a palladium(II)-catalyzed cyclization of allylic alcohol as a key reaction to achieve a total synthesis of the azasugar 1-deoxynojirimycin from o-mannitol. This reaction should be useful for the stereoselective construction of natural poly-substituted piperidine derivatives.

An efficient strategy for the synthesis of 5-hydroxyalkylbutan-4-olides from D-mannitol: Total synthesis of (-)-muricatacin

A general approach towards the synthesis of 5-hydroxyalkylbutan-4-olides from D-mannitol has been described. The approach has successfully been used for the total synthesis of (-)-muricatacin, an anti-tumor natural product.

Palladium(II)-catalyzed cyclization of urethanes and total synthesis of 1-deoxymannojirimycin.

The palladium(II)-catalyzed cyclization of the urethane 8, which was derived from D-mannitol, gave the cyclic compound 9 with excellent diastereoselectivity. During these transformations, the Pd(II) species are not reduced and thus the catalyst can recycle without its reoxidation. The cycloadduct 9 was converted to 1-deoxymannojirimycin.