114817-96-8

Basic information

• Product Name: [(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methanol
• Synonyms: [(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methanol
• CAS NO: 114817-96-8
• Molecular Weight: 158.197
• Mol File: 114817-96-8.mol
• Article Data: 21

Chemical Properties

• CAS DataBase Reference: [(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methanol(CAS DataBase Reference)
• NIST Chemistry Reference: [(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methanol(114817-96-8)
• EPA Substance Registry System: [(4R,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methanol(114817-96-8)

Safety Data

• Hazardous Substances Data: 114817-96-8(Hazardous Substances Data)

Upstream product

• 922-65-6 divinylcarbinol 
• 85963-83-3 (4R,5R)-2,2-Dimethyl-5-vinyl-1,3-dioxolan-4-carbonsaeure-methylester 
• 213767-09-0 2,3-O-isopropylidene-L-erythrofuranose 
• 56543-10-3 2,3-O-isopropylidene-D-lyxono-1,4-lactone 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 37669-01-5 2,3-O-isopropylidene-L-erythrose 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 50-69-1 D-ribose 
• 50600-40-3 (3aS,4S,6aR)-4-(iodomethyl)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxole 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 532-20-7 D-Ribose 
• 94324-23-9 5-bromo-5-deoxy-2,3-O-isopropylidene-D-ribono-1,4-lactone 
• 210702-71-9 Benzoic acid (2S,3R)-2,3-dihydroxy-pent-4-enyl ester 

Downstream Products

• 718613-98-0 C₂₀H₃₃NO₄Si 
• 718614-01-8 Acetic acid (3R,4S,5S)-2-benzyl-3-((4R,5S)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidin-4-ylmethyl ester 
• 718614-05-2 [(3R,4S,5S)-2-Benzyl-3-[(4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidin-4-yl]-methanol 
• 718613-99-1 (3R,4R,5S)-2-Benzyl-3-[(4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidine-4-carboxylic acid methyl ester 
• 718614-00-7 Acetic acid (3R,4S,5S)-2-benzyl-3-[(4R,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-5-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-isoxazolidin-4-ylmethyl ester 
• 1393792-94-3 tert-butyl (S,Z)-4,5-O-isopropylidene-4,5-dihydroxyhex-3-enoate 
• 1393792-93-2 tert-butyl (3R,4R,5S)-3-(N-benzyl-N-isopropylamino)-4,5-O-isopropylidene-4,5-dihydroxyhexanoate 
• 1393792-96-5 tert-butyl (3R,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate 
• 1393792-97-6 tert-butyl (3S,4R,5S,αS)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate 
• 1393792-99-8 tert-butyl (3R,4R,5S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate 
• 1393793-00-4 tert-butyl (3S,4R,5S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-4,5-O-isopropylidene-4,5-dihydroxyhexanoate 
• 1400679-89-1 (5S,6R,12S,E)-5,6-dihydroxy-12-methyloxacyclododec-3-en-2-one 
• 99902-66-6 4,5-dideoxy-2,3-O-isopropylidene-D-erythro-pent-4-enonic acid 
• 1393804-02-8 (3R,4S)-3,4-O-isopropylidene-2-(4-cyanobenzyl)tetrahydrofuran-3,4-diol 

Relevant articles and documents

Chiron Approaches to the Antitumor Natural Product Fuzanin D

Fuzanin D, a pyridine-containing natural product, which exhibits cytotoxic activity against DLD-1 cells, is synthesized in a concise manner using l-arabinose or ethyl l-lactate as chiral pool substrates in nine steps (14.4% overall yield) and six steps (30.8% overall yield), respectively. The key steps involve Wittig olefination and olefin cross--metathesis.

Reductive ring opening of 6-deoxy-6-iodopyranosides and 5-deoxy-5-iodofuranosides by manganese. A convenient procedure for the preparation of chiral 5-hexenals and 4-pentenals

Reaction of fully protected 6-iodopyranosides and 5-iodofuranosides with Mn in the presence of trimethylsilyl chloride and PbCl2 (Takai-conditions) afforded the corresponding 5-hexenals and 4-pentenals in good to moderate yields.

Preparation of anti -vicinal amino alcohols: Asymmetric synthesis of d - Erythro -sphinganine, (+)-spisulosine, and d - Ribo -phytosphingosine

Two variations of the Overman rearrangement have been developed for the highly selective synthesis of anti-vicinal amino alcohol natural products. A MOM ether-directed palladium(II)-catalyzed rearrangement of an allylic trichloroacetimidate was used as the key step for the preparation of the protein kinase C inhibitor d-erythro-sphinganine and the antitumor agent (+)-spisulosine, whereas the Overman rearrangement of chiral allylic trichloroacetimidates generated by the asymmetric reduction of an α,β-unsaturated methyl ketone allowed rapid access both to d-ribo-phytosphingosine and l-arabino-phytosphingosine.

Total synthesis of (+)-cladospolide A

A stereoselective total synthesis of (+)-cladospolide A from d-ribose is described. Key features of the synthesis include olefin cross metathesis and Yamaguchi lactonization. Georg Thieme Verlag Stuttgart New York.

First asymmetric total synthesis of aspergillide D

The first asymmetric total synthesis of a 16-membered macrolide, aspergillide D, is described. The chiral centers of the acid are derived from d-ribose and the alcohol subunit from 1,8-octane diol through Sharpless kinetic resolution, respectively. The other key reactions include Yamaguchi esterification, ring-closing metathesis reaction, and Shiina macrolactonization to construct the fully functionalized macrocycle.