Methanesulfonic acid (R)-1-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-methanesulfonyloxy-ethyl ester

Base Information

• Chemical Name: Methanesulfonic acid (R)-1-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-methanesulfonyloxy-ethyl ester
• CAS No.: 314061-33-1
• Molecular Formula: C₁₉H₂₈O₁₀S₂
• Molecular Weight: 480.557
• Mol file: 314061-33-1.mol

Synonyms:Methanesulfonic acid (R)-1-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-methanesulfonyloxy-ethyl ester

Chemical Property of Methanesulfonic acid (R)-1-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-methanesulfonyloxy-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methanesulfonic acid (R)-1-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-methanesulfonyloxy-ethyl ester

There total 6 articles about Methanesulfonic acid (R)-1-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-methanesulfonyloxy-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: 82.0%

methanesulfonyl chloride (124-63-0) + 3-C-(benzyloxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose (85315-68-0) → Methanesulfonic acid (R)-1-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-methanesulfonyloxy-ethyl ester (314061-33-1)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(00)01437-4

Reference yield:

O1,O2;O5,O6-diisopropylidene-3-methylene-α-D-ribo-3-deoxy-hexofuranose (21665-16-7) → Methanesulfonic acid (R)-1-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-methanesulfonyloxy-ethyl ester (314061-33-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: BH₃*SMe₂ / tetrahydrofuran

1.2: 73 percent / H₂O₂; NaOH

2.1: 90 percent / Bu₄NI / aq. NaOH

3.1: 100 percent / aq. ACOH / 40 °C

4.1: 82 percent / Et₃N / CH₂Cl₂

With dimethylsulfide borane complex; tetra-(n-butyl)ammonium iodide; acetic acid; triethylamine; In tetrahydrofuran; sodium hydroxide; dichloromethane; 1.1: hydroboration / 1.2: Oxidation / 2.1: Etherification / 3.1: Hydrolysis / 4.1: mesylation;

DOI:10.1016/S0040-4039(00)01437-4

Reference yield:

1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose (2847-00-9) → Methanesulfonic acid (R)-1-((3aR,5S,6R,6aR)-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-methanesulfonyloxy-ethyl ester (314061-33-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 60 percent / BuLi / diethyl ether

2.1: BH₃*SMe₂ / tetrahydrofuran

2.2: 73 percent / H₂O₂; NaOH

3.1: 90 percent / Bu₄NI / aq. NaOH

4.1: 100 percent / aq. ACOH / 40 °C

5.1: 82 percent / Et₃N / CH₂Cl₂

With n-butyllithium; dimethylsulfide borane complex; tetra-(n-butyl)ammonium iodide; acetic acid; triethylamine; In tetrahydrofuran; sodium hydroxide; diethyl ether; dichloromethane; 1.1: Elimination / 2.1: hydroboration / 2.2: Oxidation / 3.1: Etherification / 4.1: Hydrolysis / 5.1: mesylation;

DOI:10.1016/S0040-4039(00)01437-4

upstream raw materials:

methanesulfonyl chloride

3-C-(benzyloxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-allofuranose

((3aR,5S,6R,6aR)-tetrahydro-2,2-dimethyl-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)furo[2,3-d][1,3]dioxol-6-yl)methanol

O¹,O²;O⁵,O⁶-diisopropylidene-3-methylene-α-D-ribo-3-deoxy-hexofuranose

Downstream raw materials:

2-((3aR,5R,6R,6aR)-6-Benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethanol

3-C-(benzyloxymethyl)-3,5,6-trideoxy-1,2-O-isopropylidene-α-D-ribo-5-hexenofuranose