((3aR,4R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylbenzoate

Base Information

• Chemical Name: ((3aR,4R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylbenzoate
• CAS No.: 1000609-88-0
• Molecular Formula: C₁₅H₁₈O₆
• Molecular Weight: 294.304
• Mol file: 1000609-88-0.mol

Synonyms:((3aR,4R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylbenzoate

Chemical Property of ((3aR,4R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylbenzoate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((3aR,4R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylbenzoate

There total 4 articles about ((3aR,4R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylbenzoate 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: 90.0%

2,3-O-isopropylidene-β-D-ribofuranose (67814-68-0) + benzoyl chloride (98-88-4) → ((3aR,4R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylbenzoate (1000609-88-0)

Guidance literature:

With pyridine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1081/NCN-120037666

Reference yield: 58.0%

Benzoic acid (3aR,4S,6R,6aR)-6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester → ((3aR,4R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylbenzoate + ((3aR,4R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylbenzoate (1000609-88-0) + 1-O-benzoyl-2,3-O-isopropylidene-β-D-ribofuranose (203632-34-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1021/jo701608p

Reference yield:

6-O-benzoyl-2,3-O-isopropylidine-D-ribonolactone (131303-93-0) → ((3aR,4R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylbenzoate + ((3aR,4R,6aR)-6-hydroxy-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methylbenzoate (1000609-88-0)

Guidance literature:

With lithium triethylborohydride; In tetrahydrofuran; dichloromethane; at 0 ℃; for 0.5h; Overall yield = 85 %; Overall yield = 49 mg; chemoselective reaction;

DOI:10.1016/j.carres.2016.06.002

upstream raw materials:

2,3-O-isopropylidene-β-D-ribofuranose

benzoyl chloride

2,3-O-isopropylidene-D-ribofuranose

6-O-benzoyl-2,3-O-isopropylidine-D-ribonolactone

Downstream raw materials:

2-(5-O-benzoyl-2,3-O-isopropylidene-D-ribofuranosyl)-N-ethylmaleimide

4-(5-O-benzoyl-2,3-O-isopropylidene-D-ribofuranosyl)-1,3-dioxolan-2-one

5-O-benzoyl-2,3-O-isopropylidene-1S-(methylthio)carbonyl-1-thio-β-D-ribofuranose

1,4-anhydro-5-O-benzoyl-2,3-O-isopropylidene-D-ribitol