5987-33-7

Basic information

• Product Name: 1,5-Anhydro-2-deoxy-4-O,6-O-(phenylmethylene)-D-ribo-hexa-1-enitol
• Synonyms: 1,5-Anhydro-2-deoxy-4-O,6-O-(phenylmethylene)-D-ribo-hexa-1-enitol;Nsc287049;1,5-Anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose
• CAS NO: 5987-33-7
• Molecular Formula: C₁₃H₁₄O₄
• Molecular Weight: 234.2479
• Mol File: 5987-33-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 420.9°Cat760mmHg
• Flash Point: 208.3°C
• Appearance: /
• Density: 1.259g/cm³
• Vapor Pressure: 7.79E-08mmHg at 25°C
• Refractive Index: 1.567
• CAS DataBase Reference: 1,5-Anhydro-2-deoxy-4-O,6-O-(phenylmethylene)-D-ribo-hexa-1-enitol(CAS DataBase Reference)
• NIST Chemistry Reference: 1,5-Anhydro-2-deoxy-4-O,6-O-(phenylmethylene)-D-ribo-hexa-1-enitol(5987-33-7)
• EPA Substance Registry System: 1,5-Anhydro-2-deoxy-4-O,6-O-(phenylmethylene)-D-ribo-hexa-1-enitol(5987-33-7)

Safety Data

• Hazardous Substances Data: 5987-33-7(Hazardous Substances Data)

Usage

General Description

1,5-Anhydro-2-deoxy-4-O,6-O-(phenylmethylene)-D-ribo-hexa-1-enitol is a complex chemical compound with a long, descriptive name. It is a derivative of D-ribo-hexa-1-enitol, with a phenylmethylene group attached at the 4th and 6th positions, and a 1,5-anhydro-2-deoxy substitution. 1,5-Anhydro-2-deoxy-4-O,6-O-(phenylmethylene)-D-ribo-hexa-1-enitol is likely to have applications in organic synthesis and medicinal chemistry due to its unique structure and potential properties. However, further research and testing would be needed to fully understand its potential uses and effects.

InChI:InChI=1/C13H14O4/c14-10-6-7-15-11-8-16-13(17-12(10)11)9-4-2-1-3-5-9/h1-7,10-14H,8H2

Upstream product

• 2880-96-8 (1aR,2S,6R,7aR,7bR)-2-Methoxy-6-phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalene 
• 69534-73-2 3,4,6-O-tri-O-acetyl-D-glucal 
• 111425-49-1 phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside 
• 111425-52-6 thiophenyl 2,3-dideoxy-α-D-glucopyranoside 
• 134756-58-4 C₁₉H₁₈O₃S 
• 13035-39-7 1-deoxy-D-glucopyranoside 
• 66537-92-6 methyl 2,3-anhydro-4,6-benzylidene-α-D-allopyranoside 
• 63598-37-8 1,5-anhydro-2,3:4,6-di-O-benzylidene-D-allitol 
• 76513-66-1 Trimethyl-[2-((4aR,8S,8aS)-2-phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-8-yloxymethoxy)-ethyl]-silane 
• 14125-73-6 Methyl-4,6-O-benzyliden-2-deoxy-2-jod-α-D-altropyranosid 
• 19465-09-9 methyl 4,6-O-benzylidene-2-bromo-2-deoxy-α-D-altropyranoside 
• 925-90-6 ethylmagnesium bromide 
• 3150-15-0 methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside 
• 4416-59-5 n-decyllithium 

Downstream Products

• 1279711-50-0 3-O-benzyl-4,6-O-benzylidene-1-deoxy-1R-deutero-D-altropyranose 
• 88095-33-4 (4aR,6S,8aS)-6-Allyl-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine 
• 88095-32-3 2,6-anhydro-5,7-O-benzylidene-1,3,4-trideoxy-D-arabino-hept-3-enitol 
• 88095-34-5 (4aR,6S,8aS)-6-(2-Methyl-allyl)-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine 
• 88095-36-7 (4aR,8R,8aS)-8-(2-Methyl-allyl)-2-phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine 
• 88095-35-6 (4aR,8R,8aS)-8-Allyl-2-phenyl-4,4a,8,8a-tetrahydro-pyrano[3,2-d][1,3]dioxine 
• 18968-70-2 Methyl-4,6-O-benzyliden-β-D-erythro-hex-2-en-pyranosid 
• 127643-70-3 N-benzyl-2-carboxy-2-deoxy-β-D-altrohexopyranosylaminolactam 
• 127643-71-4 (3S,4R)-N-benzyl-3-hydroxymethyl-4-(1',3'-dihydroxyisopropoxy)-azetidinone 
• 127604-40-4 N-benzyl-4,6-O-benzylidene-2-carboxy-2-deoxy-β-D-altrohexopyranosylamino-lactam 
• 127604-39-1 4,6-O-benzylidene-3-carboxy-2-deoxy-β-D-altrohexopyranosylamino-lactam 
• 120525-41-9 3-((4aR,6R,6aS,9aS,9bS)-8-Ethoxy-2-phenyl-octahydro-furo[2',3':4,5]pyrano[3,2-d][1,3]dioxin-6-yl)-propionitrile 
• 120525-41-9 3-((4aR,6S,6aS,9aS,9bS)-8-Ethoxy-2-phenyl-octahydro-furo[2',3':4,5]pyrano[3,2-d][1,3]dioxin-6-yl)-propionitrile 
• 120525-40-8 (4aR,6S,6aS,9aS,9bS)-8-Ethoxy-2-phenyl-octahydro-furo[2',3':4,5]pyrano[3,2-d][1,3]dioxine-6-carbonitrile 

Relevant articles and documents

Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides

Glycals and 4-deoxypentenosides (4-DPs), unsaturated pyranosides with similar structures and reactivity profiles, can exhibit a high degree of stereoselectivity upon epoxidation with dimethyldioxirane (DMDO). In most cases, the glycals and their corresponding 4-DP isosteres share the same facioselectivity, implying that the pyran substituents are largely responsible for the stereodirecting effect. Fully substituted dihydropyrans are subject to a "majority rule", in which the epoxidation is directed toward the face opposite to two of the three groups. Removing one of the substituents has a variable effect on the epoxidation outcome, depending on its position and also on the relative stereochemistry of the remaining two groups. Overall, we observe that the greatest loss in facioselectivity for glycals and 4-DPs is caused by removal of the C3 oxygen, followed by the C5/anomeric substituent, and least of all by the C4/C2 oxygen. DFT calculations based on polarized-π frontier molecular orbital (PPFMO) theory support a stereoelectronic role for the oxygen substituents in 4-DP facioselectivity, but less clearly so in the case of glycals. We conclude that the anomeric oxygen in 4-DPs contributes toward a stereoelectronic bias in facioselectivity whereas the C5 alkoxymethyl in glycals imparts a steric bias, which at times can compete with the stereodirecting effects from the other oxygen substituents.

Free radical mediated reduction and deoxygenation of epoxides

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REACTION OF BUTYLLITHIUM WITH BENZYLIDENE ACETALS OF ALDOPYRANOSIDES AND 1,5-ANHYDROALDITOLS

Under suitable conditions, butyllithium selectively cleaves 5-membered benzylidene acetals (1,3-dioxolane ring) leaving the 6-membered analogs (1,3-dioxane ring) intact in aldopyranoside and 1,5-anhydroalditol derivatives.The usual course of the reaction