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

Base Information

• Chemical Name: (6-Hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate
• CAS No.: 6022-96-4
• Molecular Formula: C15H18 O6
• Molecular Weight: 294.304
• NSC Number: 127670,102633,84317,21930
• DSSTox Substance ID: DTXSID30975636
• Mol file: 6022-96-4.mol

Synonyms:5-o-benzoyl-1,2-o-(1-methylethylidene)pentofuranose;6022-96-4;NSC102633;(6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate;6612-91-5;a-D-Ribofuranose, 1,2-O-(1-methylethylidene)-, 5-benzoate;NSC84317;NCIOpen2_007129;6893-72-7;SCHEMBL13871568;DTXSID30975636;WKRBIHIDJVMVGS-UHFFFAOYSA-N;((3aS,5R,6R,6aS)-6-Hydroxy-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate;5460-57-1;NSC21930;NSC-21930;NSC-84317;NSC127670;AKOS023600040;NSC-102633;NSC-127670;Benzoic acid 6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

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

Chemical Property:

• Vapor Pressure: 3.14E-08mmHg at 25°C
• Boiling Point: 432°C at 760 mmHg
• PKA: 13.10±0.60(Predicted)
• Flash Point: 159.2°C
• PSA: 74.22000
• Density: 1.253g/cm³
• LogP: 1.08070
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 294.11033829
• Heavy Atom Count: 21
• Complexity: 390

Purity/Quality:

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

5-O-Benzoyl-1,2-O-isopropylidene-a-D-xylofuranose ^*data from reagent 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)O)C

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

There total 15 articles about (6-Hydroxy-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: 96.0%

vinyl benzoate (769-78-8,24991-32-0) + 1,2-O-isopropylidene-α-D-xylose (20031-21-4) → 5-O-benzoyl-α-D-xylofuranose (6022-96-4)

Guidance literature:

With Candida antarctica lipase B immobilized on polyacrylate; In tetrahydrofuran; at 40 ℃; for 1.16667h; Reagent/catalyst; Solvent; regioselective reaction;

DOI:10.1080/15257770.2013.847957

Reference yield: 95.0%

benzoyl chloride (98-88-4) + 1,2-O-isopropylidene-α-D-xylose (20031-21-4) → 5-O-benzoyl-α-D-xylofuranose (6022-96-4)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1080/15257779508014662

Reference yield: 95.0%

(3aR,4S,6aR)-Hexahydro-2-oxofuro-[3,4-b]furan-4-carboxaldehyde + ammonium chloride + benzoyl chloride (98-88-4) + 1,2-O-isopropylidene-α-D-xylose (20031-21-4) → 5-O-benzoyl-α-D-xylofuranose (6022-96-4)

Guidance literature:

With pyridine; copper(II) sulfate; N,N-dimethylamino-pyridine; In dichloromethane; water;

upstream raw materials:

benzoyl chloride

1,2-O-isopropylidene-α-D-xylose

D-xylofuranose

Benzoic trimethylacetic anhydride

Downstream raw materials:

O³-acetyl-O⁵-benzoyl-O¹,O²-isopropylidene-α-D-xylofuranose

5-O-benzoyl-1,2-O-isopropylidene-3-O-paratoluenesulfonyl-α-D-xylofuranose

5-O-benzoyl-3-O-methyl-1,2-O-isopropylidene-α-D-xylofuranose

1,2-O-isopropylidene-5-O-benzoyl-3-O-trifluoromethanesulfonyl-α-D-xylofuranose

Refernces

• 1、 -. "CYCLIC DINUCLEOTIDES AS STING AGONISTS". Paragraph 0086-0087. . Retrieved 2021/01/29.
• 2、 -. "SELECTIVE INHIBITOR OF PROTEIN ARGININE METHYLTRANSFERASE 5 (PRMT5)". Paragraph 00308. . Retrieved 2020/08/28.