((3aR,5S,6aR)-2,2-dimethyl-6-methylenetetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

Base Information

• Chemical Name: ((3aR,5S,6aR)-2,2-dimethyl-6-methylenetetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate
• CAS No.: 59896-02-5
• Molecular Formula: C₁₆H₁₈O₅
• Molecular Weight: 290.316
• Mol file: 59896-02-5.mol

Synonyms:((3aR,5S,6aR)-2,2-dimethyl-6-methylenetetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

Chemical Property of ((3aR,5S,6aR)-2,2-dimethyl-6-methylenetetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((3aR,5S,6aR)-2,2-dimethyl-6-methylenetetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate

There total 8 articles about ((3aR,5S,6aR)-2,2-dimethyl-6-methylenetetrahydrofuro[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: 100.0%

((3aR,5S,6aR)-2,2-dimethyl-6-methylene-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (64775-10-6) + benzoyl chloride (98-88-4) → ((3aR,5S,6aR)-2,2-dimethyl-6-methylenetetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (59896-02-5)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1016/S0968-0896(01)00266-8

Reference yield: 87.0%

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0) + Methyltriphenylphosphonium bromide (1779-49-3) → ((3aR,5S,6aR)-2,2-dimethyl-6-methylenetetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (59896-02-5)

Guidance literature:

With sodium tert-pentoxide; In tetrahydrofuran;

DOI:10.1080/15257770701521730

Reference yield: 79.0%

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0) + Methyltriphenylphosphonium bromide (1779-49-3) → ((3aR,5S,6aR)-2,2-dimethyl-6-methylene-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol (64775-10-6) + ((3aR,5S,6aR)-2,2-dimethyl-6-methylenetetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methyl benzoate (59896-02-5)

Guidance literature:

Methyltriphenylphosphonium bromide; With tert-Amyl alcohol; sodium hydride; In tetrahydrofuran; at 20 ℃; for 2h;

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/S0968-0896(01)00266-8

upstream raw materials:

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

Methyltriphenylphosphonium bromide

((3aR,5S,6aR)-2,2-dimethyl-6-methylene-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)methanol

benzoyl chloride

Downstream raw materials:

di-O-acetyl-1,2-O-benzoyl-5-desoxy-3-methylidene-3-β-D-erythro-pentofurannose

Benzoic acid (2S,4R)-4,5-dihydroxy-3-methylene-tetrahydro-furan-2-ylmethyl ester

5-O-benzoyl-3-deoxy-1,2-O-isopropylidene-3-C-methyl-α-D-erythro-pentofuranose

1,4-anhydro-5-O-benzoyl-3-deoxy-3-C-methylene-D-erythro-pentitol