15397-15-6

Basic information

• Product Name: 1,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose
• Synonyms: 2-C-Methyl-beta-D-ribofuranose 1,2,3,5-tetrabenzoate;2-C-Methyl-b-D-ribofuranose 1,2,3,5-tetrabenzoate;1,2,3,5-Tetra-O-benzoyl-2...;b-D-Ribofuranose, 2-C-Methyl-, tetrabenzoate;(2S,3R,4R,5R)-5-((benzoyloxy)Methyl)-3-Methyltetrahydrofuran-2,3,4-triyl tribenzoate;2-C-Methyl-1,2,3,5-tetra-O-benzoyl-beta-D-ribofuranose;(2S,3R,4R,5R)-2,4-bis(benzoyloxy)-5-[(benzoyloxy)methyl]-3-methyloxolan-3-yl benzoate;1,2,3,5-tera-o-benzoyl-2'-c-methyl-beta-d-ribofuranose
• CAS NO: 15397-15-6
• Molecular Formula: C₃₄H₂₈O₉
• Molecular Weight: 580.586
• EINECS: 1312995-182-4
• Product Categories: Carbohydrates & Derivatives
• Mol File: 15397-15-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 154-156 °C
• Boiling Point: 687.3 °C at 760 mmHg
• Flash Point: 286.7 °C
• Appearance: White to Off-white/Powder
• Density: 1.34
• Vapor Pressure: 9.68E-19mmHg at 25°C
• Refractive Index: 1.634
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• Solubility: Soluble in chloroform or acetonitrile
• CAS DataBase Reference: 1,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose(15397-15-6)
• EPA Substance Registry System: 1,2,3,5-Tetra-O-benzoyl-2-C-methyl-beta-D-ribofuranose(15397-15-6)

Safety Data

• Hazardous Substances Data: 15397-15-6(Hazardous Substances Data)

Usage

Chemical Properties

White Powder

Uses

1,2,3,5-Tetra-O-benzoyl-2-C-methyl-β-D-ribofuranose (cas# 15397-15-6) is a compound useful in organic synthesis.

InChI:InChI=1/C34H28O9/c1-34(43-32(38)26-20-12-5-13-21-26)28(41-30(36)24-16-8-3-9-17-24)27(22-39-29(35)23-14-6-2-7-15-23)40-33(34)42-31(37)25-18-10-4-11-19-25/h2-21,27-28,33H,22H2,1H3/t27-,28-,33+,34-/m1/s1

Upstream product

• 729596-46-7 3,5-di-O-benzoyl-2-C-methyl-D-ribono-γ-lactone 
• 30361-18-3 3,5-dibenzoyloxy-2-C-methy-β-D-ribofuranose 
• 98-88-4 benzoyl chloride 
• 30361-18-3 3,5-di-O-benzoyl-2-C-methyl-D-ribofuranose 
• 16434-48-3 1,3,5-tri-O-benzoyl-2-C-methyl-α-D-ribofuranose 
• 30361-17-2 2,3,5-tri-O-benzoyl-2-C-methyl-α/β-D-ribofuranose 
• 22224-41-5 1,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 2747-38-8 methyltrichlorotitanium 
• 157037-56-4 1,3,5-tri-O-benzoyl-2-oxo-α-D-erythro-pentofuranose 
• 75-16-1 methylmagnesium bromide 
• 7392-74-7 (3R,4R,5R)-5-((benzoyloxy)methyl)-3-methyl-2-oxotetrahydrofuran-3,4-diyl dibenzoate 
• 30361-17-2 2-methyl-2,3,5-tribenzoyl-ribonolactol 
• 492-30-8 2-C-methyl-D-ribono-1,4-lactone 

Downstream Products

• 862973-68-0 1-((2R,3R,4R,5R)-3,4-Bis-benzoyloxy-5-benzoyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-5-cyanomethyl-1H-imidazole-4-carboxylic acid methyl ester 
• 622379-84-4 C₃₂H₂₅BrN₄O₇ 
• 622379-55-9 8-(3,4-bis-benzoyloxy-5-benzoyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-2-methylsulfanyl-4,5-dioxo-3,4,5,8-tetrahydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester 
• 622379-64-0 9-(2',3',5'-tri-O-benzoyl-2'-C-methyl-β-D-ribofuranosyl)-6-methylthio-purine 
• 23643-36-9 2′,3′,5′-tri-O-benzoyl-2′-C-methyluridine 
• 622379-83-3 C₃₀H₂₅N₃O₉ 
• 15397-12-3 2'-methyl-adenosine 
• 69216-50-8 1-(2,3,5-Tri-O-benzoyl-β-D-ribofuranosyl)-3-carbamoyl-pyridinium 
• 205171-10-4 2,6-dichloro-9-(2-C-methyl-2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine 

Relevant articles and documents

Synthesis process of (2R')-2'-deoxyl-2'-fluoro-2'-methyluridine

The invention discloses a synthesis process of (2R')-2'-deoxyl-2'-fluoro-2'-methyluridine, relates to the technical field of synthesis of medicines, and solves the technical problems of high cost andlow product yield of the existing process. According to the synthesis process, sodium borohydride or potassium borohydride is used for reducing ribose lactone, so that an expensive reductive reagent which is sodium dihydro-bis-(2-methoxyethoxy)aluminate or lithium tri-tert-butoxyaluminum hydride is not used, and the cost is greatly reduced; N,O-bis(trimethylsilyl)acetamide is used as a silicon etherification reagent, so that the yield of glycosylation reaction is increased; the product yield can reach 85-90% and is far higher than that in route III by 58%; the product yield is obviously increased; hydroxyl at the 5' site is protected, so that side reaction in ring-closing reaction can be avoided; meanwhile, a common polar solvent which is dimethylformamide is used; the product yield undercatalysis of sodium hydrogen carbonate can reach 87-92%. The synthesis process is easy to operate; the process condition is more easily controlled; the cost is reduced; the synthesis process is applicable to large-batch production.

PROCESS FOR THE PREPARATION OF RIBOFURANOSE DERIVATIVES

The present invention relates to a new process in 3 steps starting from 2-C-methyl-D-ribopentono-1,4-lactone for the preparation of tetra-acyl ribofuranose derivatives of Formula (I) useful in the synthesis of nucleotides.

A short, flexible route toward 2'-C-branched ribonucleosides

A five-step synthesis of 2'-C-branched ribonucleosides from commercially obtained 1,3,5-tri-O-benzoyl-α-D-ribofuranose (4) is described. The free hydroxyl group of 4 was oxidized in high yield with Dess-Martin periodane reagent. The resultant 2-ketosugar was treated with MeMgBr/TiCl4, CH2=CHMgBr/CeCl3, or TMSC≡CLi/CeCl3, and in each case addition to the ketone proceeded stereoselectively to provide 2-alkylated ribofuranosides. After conversion to the corresponding tetrabenzoyl derivatives, the 2-alkylribofuranosides were coupled to nucleobases under Vorbruggen persilylation conditions, giving the β-nucleosides with high stereoselectivity. Deprotection with methanolic ammonia provided the title compounds in 17-49% overall yields from 4.