2,3-O-Isopropylidene-2-C-methyl-D-ribonic-gamma-lactone

Base Information

• Chemical Name: 2,3-O-Isopropylidene-2-C-methyl-D-ribonic-gamma-lactone
• CAS No.: 23709-41-3
• Molecular Formula: C9H14 O5
• Molecular Weight: 202.207
• Mol file: 23709-41-3.mol

Synonyms:Ribonicacid, 2,3-O-isopropylidene-2-C-methyl-, g-lactone, D- (6CI,8CI); Furo[3,4-d]-1,3-dioxole,D-ribonic acid deriv.

Chemical Property of 2,3-O-Isopropylidene-2-C-methyl-D-ribonic-gamma-lactone

Chemical Property:

• Melting Point: 52-54 ºC
• Boiling Point: 328 ºC
• PKA: 13.68±0.10(Predicted)
• Flash Point: 130 ºC
• PSA: 86.99000
• Density: 1.230
• LogP: -1.98400
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

98%, ^*data from raw suppliers

2-C-Methyl-2,3-O-isopropylidene-D-ribono-1,4-lactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-C-Methyl-2,3-O-isopropylidene-D-ribono-1,4-lactone is used in the synthesis of carbon-branched carbohydrate chirons: enantiomers of 2-C-Methyl-ribono-1,4-lactone (M325961) and 2-C-Methyl-arabinonolactone, as Neplanocyn A intermediates, a potential anti-HCV agent.

Technology Process of 2,3-O-Isopropylidene-2-C-methyl-D-ribonic-gamma-lactone

There total 12 articles about 2,3-O-Isopropylidene-2-C-methyl-D-ribonic-gamma-lactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2-C-methyl-D-ribono-1,4-lactone (492-30-8,7306-56-1,19774-08-4,36791-96-5,36791-97-6,53008-90-5,53008-96-1,53008-97-2,86204-17-3,86204-18-4,93636-22-7) + acetone (67-64-1) → 2-methyl-2,3-O-(1-methylethylidene)-D-ribonic acid γ-lactone (23709-41-3)

Guidance literature:

With copper(II) sulfate; In sulfuric acid;

DOI:10.1016/j.tetlet.2006.11.137

Reference yield: 99.0%

2-C-methyl-D-ribono-1,4-lactone (492-30-8,7306-56-1,19774-08-4,36791-96-5,36791-97-6,53008-90-5,53008-96-1,53008-97-2,86204-17-3,86204-18-4,93636-22-7) + 2,2-dimethoxy-propane (77-76-9) → 2-methyl-2,3-O-(1-methylethylidene)-D-ribonic acid γ-lactone (23709-41-3)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; at 30 ℃; for 60h;

DOI:10.1016/j.bmcl.2010.03.060

Reference yield: 60.0%

2-C-methyl-DL-ribono-1,4-lactone (492-30-8,7306-56-1,19774-08-4,36791-96-5,36791-97-6,53008-90-5,53008-96-1,53008-97-2,86204-17-3,86204-18-4,93636-22-7) + acetone (67-64-1) → 2,3-O-isopropylidene-2-C-methyl-DL-ribono-1,4-lactone (23709-41-3,36791-99-8,87598-90-1,93636-14-7,93636-18-1)

Guidance literature:

With copper(I) sulfate; sulfuric acid; for 7h;

DOI:10.1016/0008-6215(84)85302-1

upstream raw materials:

2-C-methyl-D-arabino-γ-lactone

2-C-methyl-D-ribono-1,4-lactone

acetone

2,2-dimethoxy-propane

Downstream raw materials:

C₁₇H₂₂O₆

C₂₂H₂₄O₅

Refernces

• 1、 Dukhan,Bosc,Peyronnet,Storer,Gosselin. "Synthesis of 2′-C-methyl-4′-thio ribonucleosides". . p. 577 - 580. Retrieved 2005.
• 2、 -. "PHOTOACID GENERATOR, PHOTORESIST COMPRISING THE PHOTOACID GENERATOR, AND COATED ARTICLE COMPRISING SAME". Paragraph 0091-0093. . Retrieved 2016/12/16.
• 3、 -. "SUBSTITUTED NUCLEOSIDES, NUCLEOTIDES AND ANALOGS THEREOF". Paragraph 1135; 1136. . Retrieved 2016/03/08.