Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

Base Information

• Chemical Name: Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester
• CAS No.: 250588-64-8
• Molecular Formula: C₁₆H₁₇NO₆
• Molecular Weight: 319.314
• Mol file: 250588-64-8.mol

Synonyms:Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

Chemical Property of Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester

There total 2 articles about Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-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: 87.0%

sodium cyanide (773837-37-9) + 5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0) → Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester (250588-64-8)

Guidance literature:

With sodium hydrogencarbonate; In diethyl ether; water;

DOI:10.1021/jo400954p

Reference yield:

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0) + sodium cyanide (143-33-9,25596-52-5) → Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester (250588-64-8)

Guidance literature:

With sodium hydrogencarbonate; In diethyl ether; water; for 4h; Ambient temperature;

DOI:10.1021/jm00094a009

Reference yield: 100.0%

acetic anhydride (108-24-7) + Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester (250588-64-8) → 1,2,3-O-triacetyl-5-O-benzoyl-3-C-cyano-α-D-ribofuranose

Guidance literature:

Benzoic acid (3aR,5R,6R,6aR)-6-cyano-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-ylmethyl ester; With trifluoroacetic acid; In water; at 20 ℃; for 4h;

acetic anhydride; With pyridine; at 20 ℃;

DOI:10.1016/j.tet.2018.07.026

upstream raw materials:

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

sodium cyanide

sodium cyanide

Downstream raw materials:

5-O-benzoyl-3-C-cyano-1,2-O-isopropylidene-3-O-mesyl-α-D-ribofuranose

(5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranose)-3-spiro-5'-(4'-amino-2'-oxazolone)

5-O-benzoyl-3-O-carbamoyl-3-C-cyano-1,2-O-isopropylidene-α-D-ribofuranose

<1-(β-D-ribofuranosyl)thymine>-3'-spiro-5''-<4''-amino-1'',2''-oxathiole 2'',2''-dioxide>