67737-48-8

Basic information

• Product Name: methyl 5-benzyloxy-β-D-ribofuranoside
• Synonyms: methyl 5-benzyloxy-β-D-ribofuranoside
• CAS NO: 67737-48-8
• Molecular Weight: 254.283
• Mol File: 67737-48-8.mol

Chemical Properties

• CAS DataBase Reference: methyl 5-benzyloxy-β-D-ribofuranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 5-benzyloxy-β-D-ribofuranoside(67737-48-8)
• EPA Substance Registry System: methyl 5-benzyloxy-β-D-ribofuranoside(67737-48-8)

Safety Data

• Hazardous Substances Data: 67737-48-8(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 532-20-7 D-Ribose 
• 189151-29-9 methyl 5-O-benzyl-2,3-O-p-methoxybenzylidene-β-D-ribofuranoside 
• 81275-41-4 methyl 5-O-benzyl-2,3-O-isopropylidene-α-D-ribofuranoside 
• 33019-63-5 (2R,3R,4R,5R)-2-benzyloxymethyl-3,4-isopropylidenedioxy-5-methoxytetrahydrofuran 
• 4099-85-8 ((3aR,4R,6R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 58763-00-1 ((3aR,4R,6S,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 1824-96-0 methyl ribofuranoside 

Downstream Products

• 67737-49-9 methyl 5-O-benzyl-α-D-ribofuranoside 
• 79063-93-7 (2R,3R,4R)-1-Benzyloxy-5-methoxy-hexane-2,3,4-triol 
• 64363-77-5 methyl 2,3,5-tri-O-benzyl-β-D-ribofuranoside 
• 81275-20-9 methyl 5-O-benzyl-2,3-di-O-methyl-β-D-ribofuranoside 
• 69603-05-0 methyl-(O⁵-benzyl-O²,O³-carbonyl-β-D-ribofuranoside) 
• 189151-47-1 methyl 3-O-allyl-5-O-benzyl-β-D-ribofuranoside 
• 131328-54-6 Methyl 2,5-di-O-benzyl-β-D-ribofuranoside 
• 191543-71-2 methyl 3,5-di-O-benzyl-α-D-ribofuranoside 
• 79064-00-9 (2R,3R,4S)-1,3,4-Tris-benzyloxy-5-methoxy-hexan-2-ol 
• 79083-29-7 (2R,3R,4R,5S)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-methoxytetrahydrofuran 
• 86861-81-6 Toluene-4-sulfonic acid (2R,3S,4R,5R)-2-benzyloxymethyl-4-hydroxy-5-methoxy-tetrahydro-furan-3-yl ester 
• 86861-80-5 Toluene-4-sulfonic acid (2R,3R,4R,5R)-5-benzyloxymethyl-4-hydroxy-2-methoxy-tetrahydro-furan-3-yl ester 
• 100350-45-6 Methyl-5-O-benzyl-3-brom-3-desoxy-2-O-dimethylcarbamoyl-β-D-xylofuranosid 
• 91102-76-0 (+)-(Methyl-5-O-benzyl-2,3-didesoxy-β-D-ribofuranosido)<2,3-b>-1,4,7,10,13,16-hexaoxacyclooctadecan 

Relevant articles and documents

Cerium ammonium nitrate: A new catalyst for regioselective protection of glycols

The regioselective introduction of a methoxymethyl (MOM) group on different type of glycols via an orthoester intermediate was investigated. The novelty presented in this study is the use of ceric ammonium nitrate instead of the previously employed camphorsulfonic acid as catalyst. The monoprotection reaction was revealed to be highly selective when the glycol moiety was in the presence of an ether functionality. Graphical abstract

Synthesis of glucopyranoside-based ligands for D-myo-inositol 1,4,5-trisphosphate receptors

Adenophostins A and B are naturally occurring glyconucleotides that interact potently with receptors for D-myo-inositol 1,4,5-trisphosphate, an important second messenger molecule in most cell types. Here we describe the design and synthesis of glucopyranoside-based analogues of adenophostin A lacking the adenine component. The key synthetic strategy involves glycosylation of selectively protected alcohols, derived from methyl β-D-ribofuranoside or 1,4-anhydroerythritol, using glycosyl donors synthesised from 2,6-di-O-benzyl-D-glucopyranose derivatives. Further elaboration and deprotection of the coupled products gave two trisphosphate analogues; methyl 3-O-α-D-glucopyranosyl-β-D-ribofuranoside 2,3′,4′-trisphosphate ("ribophostin") and (3′S,4′R)-3′-hydroxytetrahydrofuran-4′-yl α-D-glucopyranoside 3,4,3′-trisphosphosphate ("furanophostin"). The route to furanophostin was further modified to give (3′S,4′R)-3′-hydroxytetrahydrofuran-4′-yl α-D-glucopyranoside 3′-phosphate 3,4-bisphosphorothioate, the first phosphorothioate-containing adenophostin analogue.

A disaccharide polyphosphate mimic of 1D-myo-inositol 1,4,5-trisphosphate

A concise route from D-glucose and D-ribose to a potent sugar polyphosphate second messenger mimic related to adenophostin A is described; a role for the adenine base of the adenophostins is suggested.

Synthesis of methyl 2-O-allyl-(and 3-O-allyl-)5-O-benzyl-β-D-ribofuranoside

D-Ribose was converted into methyl 5-O-benzyl-β-D-ribofuranoside and this, on tin-mediated allylation, gave a mixture of the 2-O-allyl and 3-O-allyl derivatives which were separated by chromatography. The more polar isomer was characterised as the 3-O-allyl derivative after conversion via 3-O-allyl-5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose (which was also synthesised from 3-O-allyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose) into the known 5-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose. Methyl 3-O-allyl-5-O-benzyl-β-D-ribofuranoside was converted into methyl 2-O-allyl-5-O-benzyl-β-D-ribofuranoside via methyl 2-O-allyl-5-O-benzyl-3-O(prop-1-enyl)-β-D-ribofuranoside.

HIGHLY STEREOSELECTIVE C-α-D-RIBOFURANOSYLATION. REACTIONS OF D-RIBOFURANOSYL FLUORIDE DERIVATIVES WITH ENOL TRIMETHYLSILYL ETHERS AND ALLYLTRIMETHYLSILANE

2,3,5-Tri-O-methyl-D-ribofuranosyl fluoride (6), 2,3-di-O-benzyl-5-O-methyl-D-ribofuranosyl fluoride (7), and 5-O-benzyl-2,3-di-O-methyl-D-ribo-furanosyl fluoride (8) were obtained in 57 (6α, 15; and 6β, 42), 87 (7α, 22; and 7β, 65) and 85.5 (8α, 35.5; an

The Use of Grignard Reagents in the Synthesis of Carbohydrates. III. The One-way Anomerization of Methyl Glycofuranosides and the Opening of Their Furanose Rings

The anomerization of methyl glycofuranoside derivatives with methylmagnesium iodide or t-butylmagnesium bromide occurred in a one-way manner.For example, methyl 5-O-benzyl-β-D-ribofuranoside (3β) was converted into the corresponding α-anomer (3α) in a 95p