99838-68-3

Basic information

• Product Name: (2R,3S)-3-(benzyloxy)hex-5-ene-1,2-diol
• Synonyms: (2R,3S)-3-(benzyloxy)hex-5-ene-1,2-diol
• CAS NO: 99838-68-3
• Molecular Weight: 222.284
• Mol File: 99838-68-3.mol
• Article Data: 21

Chemical Properties

• CAS DataBase Reference: (2R,3S)-3-(benzyloxy)hex-5-ene-1,2-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-3-(benzyloxy)hex-5-ene-1,2-diol(99838-68-3)
• EPA Substance Registry System: (2R,3S)-3-(benzyloxy)hex-5-ene-1,2-diol(99838-68-3)

Safety Data

• Hazardous Substances Data: 99838-68-3(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 
• 400710-04-5 1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 
• 164145-69-1 1(S)-[(2R)-1,4-dioxaspiro[4.5]decanyl]-3-buten-1-ol 
• 79364-35-5 (S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 
• 87604-53-3 (2R)-3-benzyloxy-1,2-di-O-isopropylidene-5-hexen-1,2-diol 
• 87604-54-4 (R)-4-((R)-1-(benzyloxy)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxolane 
• 87604-53-3 (R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane 
• 942137-19-1 (2R)-2-[(1S)-1-(benzyloxy)-3-butenyl]-1,4-dioxaspiro[4.5]decane 

Downstream Products

• 942137-20-4 (R)-2-[(S)-1-(benzyloxy)but-3-enyl]oxirane 
• 952609-64-2 ((4S,5R)-4-benzyloxy-5-(benzyloxymethyl)-tetrahydro-furan-2-yl)methanol 
• 952609-65-3 (4S,5R)-4-benzyloxy-5-(benzyloxymethyl)-tetrahydro-furan-2-carbaldehyde 
• 952609-66-4 ethyl (E)-3-[(4S,5R)-5-(benzyloxymethyl)-4-benzyloxy-tetrahydro-furan-2-yl]-prop-2-enoate 
• 942137-21-5 C₂₅H₄₂O₂ 
• 942137-22-6 C₂₅H₄₂O 
• 99838-70-7 (2R,3S)-3-benzyloxy-1-tosyloxy-5-hexen-2-ol 
• 116444-15-6 (2R,3S)-1,3-O-dibenzyl-2-hydroxy-5-hexene 
• 344341-14-6 1-[1-[1-hydroxy-2-phenylcarbonyloxy-(1R)-ethyl]-(1S)-3-butenyloxymethyl]benzene 
• 99838-71-8 (2R,3R)-3-benzyloxy-1-tosyloxy-5-hexen-2-ol 

Relevant articles and documents

Attempts towards the synthesis of mupirocin-H

The stereoselective synthesis of segments C1-C6 (3), C7-C12 (4) of mupirocin-H has been achieved. The synthetic procedure for the C1-C6 segment includes the zinc mediated allyl Grignard reaction with Rglyceraldehyde, Swern oxidation/Witting olefination reactions and followed by Sharpless asymmetric epoxidation. The C7-C12 segment was synthesized using again Sharpless asymmetric epoxidation on mono PMB protected 2-butene-1,4-diol, followed by regioselective opening of this epoxide with trimethyl aluminium. Both segments C1-C6 (3) and C7-C12 (4) possesses the five new stereogenic centers along with trans-olefin, but in various attempts condensation of 3 and 4 segments to give C-C bond forming parent segment (2) not affirmed, hence this work constitutes the synthesis of fragments C1-C6 (3) and C7-C12 (4) of mupirocin-H. {figure presented}

Selective synthetic method of natural products Xylapyrroside A

The invention belongs to the field of chemical synthesis, and relates to a selective synthetic method of natural products Xylapyrroside A. According to the invention, (R)-(+)-2,2-dimethyl-1,3-dioxolane-4-formaldehyde is taken as an initial raw material, a Grignard reaction, hydroxy benzyl protection, acetonide protection removal, hydroxy selective tert-butyl dimethyl silicon and benzyl protection, terminal double bond epoxidation and iodo ring opening and oxidation are carried out to obtain (4S,5R)-4,5-di-benzyloxy-6-tert-butyldimethylsilyloxy-1-n-amyl iodide-2-ketone, the product is subjected to condensation with another intermediate 5-(((tetrahydro-2H-pyrans-2-group)oxygen)methyl)-1H-pyrroles-2-formaldehyde under alkaline condition, and then the product is subjected to deprotection and cyclization, and finally the target product is synthesized. The method has the advantages of simple operation and high yield, and a reagent has the advantages of low cost and easy acquisition of the raw materials.

The protecting-group directed diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction: Total synthesis and biological evaluation of zeaenol, 7-epi-zeaenol and its analogues

The stereoselective total synthesis of zeaenol and 7-epi-zeaenol is achieved in a convergent manner using Julia-Kocienski olefination, protecting group-directed intermolecular diastereoselective Nozaki-Hiyama-Kishi (NHK) reaction, De Brabander's lactoniza