103617-76-1

Basic information

• Product Name: 6-(allyloxy)hexahydrofuro[3,2-b]furan-3-ol
• Synonyms: 6-(allyloxy)hexahydrofuro[3,2-b]furan-3-ol
• CAS NO: 103617-76-1
• Molecular Weight: 186.208
• Mol File: 103617-76-1.mol

Chemical Properties

• CAS DataBase Reference: 6-(allyloxy)hexahydrofuro[3,2-b]furan-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(allyloxy)hexahydrofuro[3,2-b]furan-3-ol(103617-76-1)
• EPA Substance Registry System: 6-(allyloxy)hexahydrofuro[3,2-b]furan-3-ol(103617-76-1)

Safety Data

• Hazardous Substances Data: 103617-76-1(Hazardous Substances Data)

Upstream product

• 106-95-6 allyl bromide 
• 652-67-5 Isosorbide 
• 641-74-7 (3S,3aS,6S,6aS)hexahydrofuro[3,2-b]furan-3,6-diol 
• 124508-14-1 1,4:3,6-dianhydro-L-glucitol 

Downstream Products

• 246530-90-5 (2'S)-2-O-[2'-(benzyloxycarbonylamino)-methyl propionate-3'-yl]-5-O-(3''-hydroxy-prop-1''-yl)-1,4:3,6-dianhydro-D-sorbitol 
• 246530-88-1 (2'S)-2-O-[2'-(benzyloxycarbonylamino)-methyl propionate-3'-yl]-5-O-(2''-hydroxy-eth-1''-yl)-1,4:3,6-dianhydro-D-sorbitol 
• 246530-85-8 (2'S)-5-O-allyl-2-O-[2'-(benzyloxycarbonylamino)-methyl propionate-3'-yl]-1,4:3,6-dianhydro-D-sorbitol 

Relevant articles and documents

Selective alkylations of 1,4:3,6-dianhydro-D-glucitol (isosorbide)

Each of the two hydroxyl groups of isosorbide can be alkylated selectively, either by direct alkylation with benzyl chloride or allyl bromide according to the reaction conditions, or by a three-step procedure involving selective monoacetylation, alkylation with four different reagents, and finally deacetylation.Monobutyl and monomethyl derivatives from isosorbide are also described.

Selective Syntheses and Properties of Anionic Surfactants Derived from Isosorbide

Two series of anionic surfactants (endo-5-O-alkyl isosorbide-2-O-propyl sulfonic acid sodium salt and exo-2-O-alkyl isosorbide-5-O-propyl sulfonic acid sodium salt) with straight alkyl chains (hexyl, octyl, decyl, and dodecyl) were synthesized from isosorbide derived from biomass, through steps of allylation, alkylation, and sulfonation. The selectivity and efficiency of the reactions were optimized by adjusting the solvent, catalyst, reactant molar ratio, and temperature. The product 2-O-allyl isosorbide was obtained with a yield of 81% and selectivity of 23:1 (endo:exo), and 2-O-alkyl isosorbide was obtained with a yield of 72% and selectivity of 24:1 (exo:endo). The synthesized anionic surfactants were characterized using the critical micelle concentration (CMC), surface activity, emulsion stability, foaming height, and the Turbiscan Stability Index. The CMC decreased with increasing alkyl chain length. The properties of endo form and exo form were compared.

Organic nitrates. O-(2,3-dihydroxypropyl)-1,4:3,6-dianhydro-hexitol-nitrates

Several hybrid molecules have been synthesized which contain both the 1,4:3,6-dianhydro-hexitol (isohexide) and glycerol partial structures, with nitrate ester gruops at different positions. Alkylation of the isohexide ring system with suitable 3-carbon units generates compounds with the 2,3-epoxypropyl side chain as key intermediates. Ring opening of these oxiranes under various conditions yield primary and secondary nitrates as well as dinitrates. Pharmacological screening shows that the new structures are much less active than the parent compounds.