((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

Base Information

• Chemical Name: ((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol
• CAS No.: 72402-14-3
• Molecular Formula: C₉H₁₆O₅
• Molecular Weight: 204.223
• Hs Code.: 2932990090
• European Community (EC) Number: 966-137-1
• DSSTox Substance ID: DTXSID10466133
• Nikkaji Number: J1.380.344G
• Mol file: 72402-14-3.mol

Synonyms:72402-14-3;Methyl-2,3-O-isopropylidene-D-ribofuranoside;((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol;Methyl 2,3-O-isopropylidene-D-ribofuranoside;[(3aR,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methanol;[(3aR,4R,6aR)-6-methoxy-2,2-dimethyl-tetrahydro-2H-furo[3,4-d][1,3]dioxol-4-yl]methanol;MFCD00038805;[(3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]methanol;Methyl 2,3-O-Isopropylidene-b-D-ribofuranoside;SCHEMBL383401;DTXSID10466133;DXBHDBLZPXQALN-XDTPYFJJSA-N;AMY30993;AKOS025291263;AS-34843;CS-0053057;methyl 2,3-o-isopropylidene--d-ribofuranoside;EN300-7372904;A866269;W-203631;((3ar,4r,6ar)-6-methoxy-2,2-dimethyltetrahydro-2h-furo[3,4-d][1,3]dioxol-4-yl)methanol;((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-methanol

Chemical Property of ((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

Chemical Property:

• Boiling Point: 72-75 °C(Press: 0.6 Torr)
• PKA: 14.14±0.10(Predicted)
• PSA: 57.15000
• Density: 1.23±0.1 g/cm3(Predicted)
• LogP: -0.12990
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 204.09977361
• Heavy Atom Count: 14
• Complexity: 217

Purity/Quality:

98%, ^*data from raw suppliers

Methyl 2,3-O-isopropylidene-D-ribofuranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(OC(C2O1)OC)CO)C
• Isomeric SMILES: CC1(O[C@@H]2[C@H](OC([C@@H]2O1)OC)CO)C
• Uses: Methyl 2,3-O-Isopropylidene-D-ribofuranoside can be prepared to use as PRMT5 inhibitors.

Technology Process of ((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

There total 19 articles about ((3aR,4R,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 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: 99.0%

methanol (67-56-1) + D-Ribose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) + acetone (67-64-1) → methyl 2,3-O-isopropylidene-D-ribofuranoside (4099-85-8,5531-21-5,20672-63-3,20672-65-5,58763-00-1,63029-07-2,72402-14-3,84894-45-1,129263-68-9,828937-29-7)

Guidance literature:

With thionyl chloride; at 10 - 25 ℃; for 24h;

Reference yield: 95.0%

methanol (67-56-1) + D-Ribose (532-20-7,613-83-2,7261-25-8,7687-39-0,13221-22-2,14795-83-6,15761-67-8,20074-49-1,25545-03-3,25545-04-4,32445-75-3,34436-17-4,36441-93-7,36468-53-8,37110-85-3,37388-49-1,38029-69-5,40461-77-6,40461-89-0,41546-19-4,41546-20-7,41546-21-8,41546-26-3,41546-29-6,41546-30-9,41546-31-0,126872-16-0,131064-98-7) + 2,2-dimethoxy-propane (77-76-9) → methyl 2,3-O-isopropylidene-D-ribofuranoside (4099-85-8,5531-21-5,20672-63-3,20672-65-5,58763-00-1,63029-07-2,72402-14-3,84894-45-1,129263-68-9,828937-29-7)

Guidance literature:

D-Ribose; 2,2-dimethoxy-propane; With perchloric acid; In water; acetone; at 0 - 20 ℃;

methanol; In water; acetone; at 20 ℃; for 2h;

DOI:10.1016/j.tetasy.2010.01.010

Reference yield: 95.0%

methanol (67-56-1) + D-ribose (50-69-1) + acetone (67-64-1) → methyl 2,3-O-isopropylidene-D-ribofuranoside (4099-85-8,5531-21-5,20672-63-3,20672-65-5,58763-00-1,63029-07-2,72402-14-3,84894-45-1,129263-68-9,828937-29-7)

Guidance literature:

With sulfuric acid; at 0 - 20 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.tetasy.2011.04.012

upstream raw materials:

methanol

D-Ribose

2,2-dimethoxy-propane

acetone

Downstream raw materials:

N⁴-Benzoyl-1-(2,3-O-isopropylidene-α-D-ribofuranosyl)-cytosine

4-N-benzoyl-2',3'-O-isopropylidenecytidine

1-O-methyl-5-O-benzyl-2,3-O-isopropylidene-D-ribofuranoside

5-O-benzoyl-2,3-isopropylidene-1-methoxy-D-ribofuranoside

Refernces

• 1、 -. "BIOMARKER PANEL TARGETED TO DISEASES DUE TO MULTIFACTORIAL ONTOLOGY OF GLYCOCALYX DISRUPTION". Paragraph 0292; 0306. . Retrieved 2021/04/02.
• 2、 Boger, Dale L.,Chanda, Prem B.,Chowdari, Naidu S.,Gangwar, Sanjeev,Gartshore, Christopher,Momirov, Jelena,Sarkar, Anindya,Tadano, Shinji,Vite, Gregory D.,Zhang, Qian. "Total Synthesis of Meayamycin and O-Acyl Analogues". . . Retrieved 2020/11/18.