Trifluoro-methanesulfonic acid (2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester
• CAS No.: 172427-40-6
• Molecular Formula: C₁₉H₂₅F₃O₈S
• Molecular Weight: 470.464

Synonyms:Trifluoro-methanesulfonic acid (2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

Chemical Property of Trifluoro-methanesulfonic acid (2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

Chemical Property:

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Technology Process of Trifluoro-methanesulfonic acid (2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

There total 13 articles about Trifluoro-methanesulfonic acid (2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-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: 94.0%

trifluoromethylsulfonic anhydride (358-23-6) + ((2R,3R,4S,4aS,8aS)-4-Benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-yl)-methanol → Trifluoro-methanesulfonic acid (2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester (172427-40-6)

Guidance literature:

With 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane; at -20 ℃;

DOI:10.1016/0040-4039(95)01973-L

Reference yield:

1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene (81972-19-2) → Trifluoro-methanesulfonic acid (2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester (172427-40-6)

Guidance literature:

Multi-step reaction with 13 steps

1: 1.) 9-BBN, 2.) 30percent H₂O₂ / 1.) THF, RT; 2.) 3M NaOH, RT

2: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

3: H₂ / Pd(OH)2/C / ethyl acetate; methanol / Ambient temperature

4: p-TsOH / CH₂Cl₂; dimethylformamide / Ambient temperature

5: 90 percent / KH / tetrahydrofuran / Ambient temperature

6: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / from -78 deg C to RT

7: L-Selectride / CH₂Cl₂ / -78 °C

8: 94 percent / NaH, TBAI / dimethylformamide

9: p-TsOH / CH₂Cl₂; methanol / Ambient temperature

10: i-Pr₂NEt / CH₂Cl₂ / Ambient temperature

11: NaH / dimethylformamide / Ambient temperature

12: PPTS / CH₂Cl₂; methanol

13: 94 percent / 2,6-di-t-butyl-4-methylpyridine / CH₂Cl₂ / -20 °C

With dmap; 9-borabicyclo[3.3.1]nonane dimer; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; hydrogen; dihydrogen peroxide; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydride; L-Selectride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(95)01973-L

Reference yield:

3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-1-propanol (173829-80-6) → Trifluoro-methanesulfonic acid (2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester (172427-40-6)

Guidance literature:

Multi-step reaction with 12 steps

1: Et₃N, DMAP / CH₂Cl₂ / Ambient temperature

2: H₂ / Pd(OH)2/C / ethyl acetate; methanol / Ambient temperature

3: p-TsOH / CH₂Cl₂; dimethylformamide / Ambient temperature

4: 90 percent / KH / tetrahydrofuran / Ambient temperature

5: (COCl)2, DMSO, Et₃N / CH₂Cl₂ / from -78 deg C to RT

6: L-Selectride / CH₂Cl₂ / -78 °C

7: 94 percent / NaH, TBAI / dimethylformamide

8: p-TsOH / CH₂Cl₂; methanol / Ambient temperature

9: i-Pr₂NEt / CH₂Cl₂ / Ambient temperature

10: NaH / dimethylformamide / Ambient temperature

11: PPTS / CH₂Cl₂; methanol

12: 94 percent / 2,6-di-t-butyl-4-methylpyridine / CH₂Cl₂ / -20 °C

With dmap; 2,6-di-tert-butyl-4-methylpyridine; oxalyl dichloride; hydrogen; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; potassium hydride; L-Selectride; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/0040-4039(95)01973-L

upstream raw materials:

trifluoromethylsulfonic anhydride

1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranos-1-yl)-2-propene

(2R,4aR,8aS,9S,9aR,10aS)-9-Benzyloxy-2-phenyl-octahydro-1,3,8,10-tetraoxa-anthracene

Toluene-4-sulfonic acid 3-((2R,4aR,6S,7R,8R,8aS)-7,8-dihydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-propyl ester

Downstream raw materials:

C₄₄H₆₄O₁₁Si

(2R,3R,4S,4aS,6S,7S,8aS)-4,7-Bis-benzyloxy-6-[(E)-3-((2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propenyl]-3-methoxy-2-methoxymethyl-octahydro-pyrano[3,2-b]pyran

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