Benzoic acid (R)-2-methanesulfonyloxy-2-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester

Base Information

• Chemical Name: Benzoic acid (R)-2-methanesulfonyloxy-2-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester
• CAS No.: 290334-83-7
• Molecular Formula: C₂₀H₂₈O₉S
• Molecular Weight: 444.503
• Mol file: 290334-83-7.mol

Synonyms:Benzoic acid (R)-2-methanesulfonyloxy-2-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester

Chemical Property of Benzoic acid (R)-2-methanesulfonyloxy-2-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (R)-2-methanesulfonyloxy-2-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester

There total 4 articles about Benzoic acid (R)-2-methanesulfonyloxy-2-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl 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: 95.0%

methanesulfonyl chloride (124-63-0) + 6-O-benzoyl-1,2:3,4-di-O-isopropylidene-D-mannitol (290836-45-2) → Benzoic acid (R)-2-methanesulfonyloxy-2-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester (290334-83-7)

Guidance literature:

With triethylamine; In dichloromethane; at -80 - -20 ℃; for 12h;

DOI:10.1016/S0040-4039(00)00749-8

Reference yield:

1,2:3,4-di-O-isopropylidene-D-mannitol (38145-93-6) → Benzoic acid (R)-2-methanesulfonyloxy-2-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester (290334-83-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / DMAP; pyridine / CH₂Cl₂ / 4 h / -80 - -20 °C

2: triethylamine / CH₂Cl₂ / 10 h / -80 - -20 °C

With pyridine; dmap; triethylamine; In dichloromethane;

DOI:10.1021/jo0269058

Reference yield:

mannitol triacetonide (3969-59-3) → Benzoic acid (R)-2-methanesulfonyloxy-2-((4R,5S,4'R)-2,2,2',2'-tetramethyl-[4,4']bi[[1,3]dioxolanyl]-5-yl)-ethyl ester (290334-83-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 8.5 g / concentrated HCl / aq. ethanol / 1 h / 45 °C

2: 83 percent / DMAP; pyridine / CH₂Cl₂ / 4 h / -80 - -20 °C

3: triethylamine / CH₂Cl₂ / 10 h / -80 - -20 °C

With pyridine; hydrogenchloride; dmap; triethylamine; In ethanol; dichloromethane;

DOI:10.1021/jo0269058

upstream raw materials:

methanesulfonyl chloride

6-O-benzoyl-1,2:3,4-di-O-isopropylidene-D-mannitol

1,2:3,4-di-O-isopropylidene-D-mannitol

mannitol triacetonide

Downstream raw materials:

4-(1-benzyloxypentyl)-2,2-dimethyl-5-oxiranyl[1,3]dioxolane

1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]ethane-1,2-diol

5-benzyloxy-1,2:3,4-di-O-isopropylidenenonane

1-[5-(1-benzyloxypentyl)-2,2-dimethyl[1,3]dioxolan-4-yl]pent-4-en-1-ol