Methanesulfonic acid (3aR,4R,6R,6aR)-6-[(S)-2-benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester

Base Information

• Chemical Name: Methanesulfonic acid (3aR,4R,6R,6aR)-6-[(S)-2-benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester
• CAS No.: 302917-28-8
• Molecular Formula: C₃₂H₄₂O₁₂S
• Molecular Weight: 650.744

Synonyms:Methanesulfonic acid (3aR,4R,6R,6aR)-6-[(S)-2-benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester

Chemical Property of Methanesulfonic acid (3aR,4R,6R,6aR)-6-[(S)-2-benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester

Chemical Property:

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Technology Process of Methanesulfonic acid (3aR,4R,6R,6aR)-6-[(S)-2-benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester

There total 10 articles about Methanesulfonic acid (3aR,4R,6R,6aR)-6-[(S)-2-benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-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: 65.0%

methanesulfonyl chloride (124-63-0) + {(3aR,4R,6S,6aR)-6-[(S)-2-Benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-methanol (302917-26-6) → Methanesulfonic acid (3aR,4R,6R,6aR)-6-[(S)-2-benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (302917-28-8)

Guidance literature:

With TEA; In dichloromethane; at 20 ℃;

DOI:10.1016/S0960-894X(00)00349-8

Reference yield:

[(2R,3R,4R)-3,4-diacetoxy-5-chlorotetrahydrofuran-2-yl]methyl acetate (40554-98-1) → Methanesulfonic acid (3aR,4R,6R,6aR)-6-[(S)-2-benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (302917-28-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / Hg(CN)2; MS 4A / CH₂Cl₂ / 20 °C

2: MeONa; MeOH / 20 °C

3: PTSA; acetone / 20 °C

4: 65 percent / TEA / CH₂Cl₂ / 20 °C

With methanol; TEA; sodium methylate; mercury(II) cyanide; toluene-4-sulfonic acid; acetone; In dichloromethane; 1: Condensation / 2: Deacetylation / 3: ketalization / 4: Mesylation;

DOI:10.1016/S0960-894X(00)00349-8

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose (57099-04-4) → Methanesulfonic acid (3aR,4R,6R,6aR)-6-[(S)-2-benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl ester (302917-28-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: Bu₂SnO / toluene

1.2: CsF / dimethylformamide / 20 °C

2.1: DEAD; PPh₃ / toluene

3.1: MeONa; MeOH

4.1: 86 percent / Hg(CN)2; MS 4A / CH₂Cl₂ / 20 °C

5.1: MeONa; MeOH / 20 °C

6.1: PTSA; acetone / 20 °C

7.1: 65 percent / TEA / CH₂Cl₂ / 20 °C

With methanol; TEA; sodium methylate; mercury(II) cyanide; di(n-butyl)tin oxide; toluene-4-sulfonic acid; triphenylphosphine; acetone; diethylazodicarboxylate; In dichloromethane; toluene; 1.1: Condensation / 1.2: benzylation / 2.1: Esterification / 3.1: Deacetylation / 4.1: Condensation / 5.1: Deacetylation / 6.1: ketalization / 7.1: Mesylation;

DOI:10.1016/S0960-894X(00)00349-8

upstream raw materials:

methanesulfonyl chloride

{(3aR,4R,6S,6aR)-6-[(S)-2-Benzyloxy-1-((3aR,5R,6R,6aR)-6-benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-ethoxy]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-methanol

[(2R,3R,4R)-3,4-diacetoxy-5-chlorotetrahydrofuran-2-yl]methyl acetate

3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose

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