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

Base Information

• Chemical Name: Methanesulfonic acid 3-benzyloxy-2-[(3aR,5R,6R,6aR)-6-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-propyl ester
• CAS No.: 98039-14-6
• Molecular Formula: C₂₇H₃₆O₉S
• Molecular Weight: 536.643

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

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

There total 10 articles about Methanesulfonic acid 3-benzyloxy-2-[(3aR,5R,6R,6aR)-6-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-propyl 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: 80.0%

methanesulfonyl chloride (124-63-0) + 3-Benzyloxy-2-[(3aR,5R,6R,6aR)-6-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-propan-1-ol (86654-50-4,86708-02-3) → Methanesulfonic acid 3-benzyloxy-2-[(3aR,5R,6R,6aR)-6-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-propyl ester (98039-14-6,98039-15-7)

Guidance literature:

With triethylamine; In benzene; at 0 - 20 ℃; for 0.25h;

DOI:10.1039/P19850000019

Reference yield:

((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 (69832-48-0) → Methanesulfonic acid 3-benzyloxy-2-[(3aR,5R,6R,6aR)-6-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-propyl ester (98039-14-6,98039-15-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 93.4 percent / NaH / dimethylsulfoxide; tetrahydrofuran / 2 h / Ambient temperature

2: 86.5 percent / 2 percent H₂SO₄ / methanol / 15 h / Ambient temperature

3: 66.8 percent / pyridine / Ambient temperature

4: 94 percent / K₂CO₃ / methanol / 0.67 h / Ambient temperature

5: 58 percent / NaH, DMSO / tetrahydrofuran / 40 h / Ambient temperature

6: 82 percent / PCC, molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / Ambient temperature

7: 78 percent / tetrahydrofuran; dimethylsulfoxide / 8 h / Ambient temperature

8: 1.) 1M BH₃; 2.) 3M NaOH, 30 percent H₂O₂ / tetrahydrofuran / Ambient temperature; 1.) 4 h; 2.) 30 min

9: 80 percent / Et₃N / benzene / 0.25 h / 0 - 20 °C

With sodium hydroxide; 4 A molecular sieve; sulfuric acid; borane; dihydrogen peroxide; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide; benzene;

DOI:10.1039/P19850000019

Reference yield:

3-deoxy-1,2,5,6-di-O-isopropylidene-3-C-(4-metoxybenzyloxymethyl)-α-D-allofuranose (98039-10-2) → Methanesulfonic acid 3-benzyloxy-2-[(3aR,5R,6R,6aR)-6-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-propyl ester (98039-14-6,98039-15-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 86.5 percent / 2 percent H₂SO₄ / methanol / 15 h / Ambient temperature

2: 66.8 percent / pyridine / Ambient temperature

3: 94 percent / K₂CO₃ / methanol / 0.67 h / Ambient temperature

4: 58 percent / NaH, DMSO / tetrahydrofuran / 40 h / Ambient temperature

5: 82 percent / PCC, molecular sieves 4 Angstroem / CH₂Cl₂ / 3 h / Ambient temperature

6: 78 percent / tetrahydrofuran; dimethylsulfoxide / 8 h / Ambient temperature

7: 1.) 1M BH₃; 2.) 3M NaOH, 30 percent H₂O₂ / tetrahydrofuran / Ambient temperature; 1.) 4 h; 2.) 30 min

8: 80 percent / Et₃N / benzene / 0.25 h / 0 - 20 °C

With sodium hydroxide; 4 A molecular sieve; sulfuric acid; borane; dihydrogen peroxide; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; pyridine; methanol; dichloromethane; dimethyl sulfoxide; benzene;

DOI:10.1039/P19850000019

upstream raw materials:

methanesulfonyl chloride

3-Benzyloxy-2-[(3aR,5R,6R,6aR)-6-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-propan-1-ol

((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

3-deoxy-1,2,5,6-di-O-isopropylidene-3-C-(4-metoxybenzyloxymethyl)-α-D-allofuranose

Downstream raw materials:

(3aR,5R,6R,6aR)-5-(2-Benzyloxy-1-methyl-ethyl)-6-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

(2R,3R,4R)-1-benzyloxy-3-hydroxy-4-hydroxymethyl-5-(4-methoxybenzyloxy)-2-methylpentane

(2S,3R,4R)-1-benzyloxy-3-hydroxy-5-(4-methoxybenzyloxy)-2,4-dimethylpentane

(2R,3R,4ξ)-5-benzyloxy-3-formyloxy-2-(4-methoxy-benzyloxymethyl)-4-methylpentanal

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