Benzoic acid (1R,2R,4R,5R)-4-[1,3]dioxolan-2-yl-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (1R,2R,4R,5R)-4-[1,3]dioxolan-2-yl-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester
• CAS No.: 258336-08-2
• Molecular Formula: C₁₅H₁₆O₆
• Molecular Weight: 292.288

Synonyms:Benzoic acid (1R,2R,4R,5R)-4-[1,3]dioxolan-2-yl-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester

Chemical Property of Benzoic acid (1R,2R,4R,5R)-4-[1,3]dioxolan-2-yl-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester

Chemical Property:

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Technology Process of Benzoic acid (1R,2R,4R,5R)-4-[1,3]dioxolan-2-yl-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester

There total 1 articles about Benzoic acid (1R,2R,4R,5R)-4-[1,3]dioxolan-2-yl-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester 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: 62.0%

Potassium benzoate (582-25-2) + 2,5-anhydro-3,6-di-O-methanesulfonyl-D-glucose ethylene acetal (157506-35-9) → Benzoic acid (1R,2R,4R,5R)-4-[1,3]dioxolan-2-yl-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester (258336-08-2)

Guidance literature:

In N,N-dimethyl-formamide; at 95 - 98 ℃; for 22h;

DOI:10.1016/S0040-4039(99)01952-8

Reference yield: 34.0%

benzoyl chloride (98-88-4) + Benzoic acid (1R,2R,4R,5R)-4-[1,3]dioxolan-2-yl-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester (258336-08-2) → C22H21N3O7 + 2,5-anhydro-3,4,6-tri-O-benzoyl-D-gulose ethylene acetal

Guidance literature:

Benzoic acid (1R,2R,4R,5R)-4-[1,3]dioxolan-2-yl-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester; With trimethylsilyl cyanide; boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃;

benzoyl chloride; With pyridine;

DOI:10.1016/j.bmcl.2012.08.093

Reference yield: 29.0%

benzoyl chloride (98-88-4) + Benzoic acid (1R,2R,4R,5R)-4-[1,3]dioxolan-2-yl-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester (258336-08-2) → 2,5-anhydro-3,4,6-tri-O-benzoyl-D-gulose ethylene acetal + C22H21ClO7 (1409941-17-8)

Guidance literature:

Benzoic acid (1R,2R,4R,5R)-4-[1,3]dioxolan-2-yl-3,6-dioxa-bicyclo[3.1.0]hex-2-ylmethyl ester; With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 46h;

With triethylamine; In dichloromethane; water;

benzoyl chloride; With pyridine; at 0 - 20 ℃; for 96h;

DOI:10.1016/j.ejmech.2019.111712

upstream raw materials:

Potassium benzoate

2,5-anhydro-3,6-di-O-methanesulfonyl-D-glucose ethylene acetal

Downstream raw materials:

Toluene-4-sulfonic acid (2S,4R,5R)-5-[1,3]dioxolan-2-yl-4-hydroxy-tetrahydro-furan-2-ylmethyl ester

C₁₅H₁₈O₇

C₂₇H₂₂O₈

(2,3,5-tri-O-benzoyl-β-D-xylofuranosyl)cyanide

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