(6-Methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

Base Information

• Chemical Name: (6-Methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate
• CAS No.: 10300-20-6
• Molecular Formula: C16H20O6
• Molecular Weight: 308.331
• NSC Number: 102632
• DSSTox Substance ID: DTXSID10295526
• Mol file: 10300-20-6.mol

Synonyms:10300-20-6;(6-methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate;5-O-Benzoyl-1,2-O-isopropylidene-3-O-Methyl-alpha-D-ribofuranose;5-o-benzoyl-3-o-methyl-1,2-o-(1-methylethylidene)pentofuranose;NSC102632;3-O-Methyl-1,2-O-(1-methylethylidene)-alpha-D-ribofuranose benzoate;SCHEMBL24686427;DTXSID10295526;NSC-102632;A900272

Chemical Property of (6-Methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

Chemical Property:

• Vapor Pressure: 2.34E-06mmHg at 25°C
• Boiling Point: 392.1°Cat760mmHg
• Flash Point: 171.5°C
• PSA: 63.22000
• Density: 1.24g/cm³
• LogP: 1.73480
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 308.12598835
• Heavy Atom Count: 22
• Complexity: 403

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(OC2C(C(OC2O1)COC(=O)C3=CC=CC=C3)OC)C

Technology Process of (6-Methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

There total 9 articles about (6-Methoxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate 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: 95.0%

((3aR,5R,65,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (6612-91-5) + methyl iodide (74-88-4) → 5-O-benzoyl-1,2-O-isopropylidene-3-O-methyl-α-D-ribofuranose (10300-20-6)

Guidance literature:

With silver(l) oxide; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 5h; Inert atmosphere;

DOI:10.3390/md17040226

Reference yield: 88.0%

C25H34O5Si + benzoyl chloride (98-88-4) → 5-O-benzoyl-1,2-O-isopropylidene-3-O-methyl-α-D-ribofuranose (10300-20-6)

Guidance literature:

C₂₅H₃₄O₅Si; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 4h;

benzoyl chloride; With triethylamine; In dichloromethane; for 1h;

Reference yield:

1,2-O-isopropylidene-α-D-xylose (20031-21-4) → 5-O-benzoyl-1,2-O-isopropylidene-3-O-methyl-α-D-ribofuranose (10300-20-6)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 4 h / 20 °C

2: Dess-Martin periodane / dichloromethane / 5 h / 20 °C

3: sodium tetrahydroborate / methanol / 3 h / 20 °C

4: sodium hydride / N,N-dimethyl-formamide / 0 °C

With pyridine; sodium tetrahydroborate; sodium hydride; Dess-Martin periodane; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.cclet.2013.03.014

upstream raw materials:

((3aR,5R,65,6aR)-6-hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

methyl iodide

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose

5-O-benzoyl-α-D-xylofuranose

Downstream raw materials:

5-O-benzoyl-1,2-O-diacetyl-3-O-methyl-β-D-ribofuranose

5-O-benzoyl-1,2-O-diacetyl-3-O-methyl-α-D-ribofuranose

5-O-benzoyl-1,2-O-diacetyl-3-O-methyl-α/β-D-ribofuranose

Refernces

• 1、 -. "CYCLIC DI-NUCLEOTIDE COMPOUNDS AND METHODS OF USE". . . Retrieved 2017/10/11.
• 2、 Tong,Lee,Goodman. "Synthesis of some 3'-O-methyl purine ribonucleosides.". . p. 1984 - 1986. Retrieved 2007/10/10.