562823-59-0

Basic information

• Product Name: (S)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-4-en-2-ol
• Synonyms: (S)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-4-en-2-ol
• CAS NO: 562823-59-0
• Molecular Weight: 306.402
• Mol File: 562823-59-0.mol

Chemical Properties

• CAS DataBase Reference: (S)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-4-en-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-4-en-2-ol(562823-59-0)
• EPA Substance Registry System: (S)-1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-4-en-2-ol(562823-59-0)

Safety Data

• Hazardous Substances Data: 562823-59-0(Hazardous Substances Data)

Upstream product

• 114826-50-5 (4R,5S)-2,2-dimethyl-4-iodomethyl-5-benzyloxymethyl-1,3-dioxolane 
• 78469-77-9 (4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane 
• 50622-09-8 2,3-O-isopropylidene-L-threitol 
• 37031-29-1 (-)-dimethy-2,3-O-isopropylidene-L-tartrate 
• 562823-57-8 [2-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethoxy]-tert-butyl-diphenyl-silane 
• 562823-69-2 (2R,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-2,3-dihydroxy-pentanoic acid ethyl ester 
• 562823-70-5 (4R,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester 
• 562823-56-7 {(4S,5S)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-methanol 
• 562823-71-6 2-((4S,5S)-5-(benzyloxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanol 
• 562823-58-9 2-((4S,5S)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)acetaldehyde 
• 256494-25-4 (E)-ethyl 5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-enoate 
• 100-39-0 benzyl bromide 
• 1054661-39-0 1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-4-en-2-one 
• 562823-72-7 1-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-pent-4-en-2-ol 

Downstream Products

• 562823-60-3 Acrylic acid (S)-1-((4S,5S)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-but-3-enyl ester 
• 562823-66-9 (2S,3S,5S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-hexanoic acid methyl ester 
• 562823-65-8 (Z)-(S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-5-(tert-butyl-dimethyl-silanyloxy)-hex-2-enoic acid methyl ester 
• 562823-61-4 (S)-6-((4S,5S)-5-Benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-5,6-dihydro-pyran-2-one 

Relevant articles and documents

Enantioselective Total Synthesis of the Proposed Structure of the Endophytic Fungal Metabolite Phomolide G: Structural Revision and Unambiguous Stereochemical Assignment

A total synthesis of the proposed structure of the natural macrolactone phomolide G (1) by a bidirectional strategy from L-tartaric acid is reported. The ω-terminus of the molecule was elaborated by nitrile extension, C3-alkylation and a substrate-controlled 1,3-ketone reduction. The α-terminus was extended by a C2aldehyde-to-alkenal homologation followed by an auxiliary controlled aldol reaction. Macrolactonization and deprotection yielded compound 1 (confirmed by X-ray analysis). This putative structure of phomolide G displayed discordant NMR spectroscopic data in comparison with those of the natural product. Detailed inspection of all NMR spectroscopic data available indicated phomolide G to be likely a diastereomer of 1. The synthetic strategy developed allows control of the absolute stereochemistry at all four chiral secondary alcohol groups. Further manipulation allowed for the preparation of diastereomer 33, the1H and13C NMR spectroscopic data of which are in full accord with that reported for the natural product.

An enantioselective synthesis of the C1-C9 segment of antitumor macrolide peloruside A

A stereocontrolled synthesis of the C1-C9 segment of the marine natural product peloruside A is described. The key steps involve Sharpless's catalytic asymmetric dihydroxylation reaction, a chelation-controlled reduction of chiral β-alkoxy ketones to elaborate the syn-1,3-diol functionality and a ring-closing olefin metathesis of a homoallylic alcohol-derived acrylate ester to form an α,β-unsaturated δ-lactone.