(R_S)-5-benzyloxy-5-hydroxymethyl-2-methoxy-2-(p-toluenesulfinyl-methyl)tetrahydropyran

Base Information

• Chemical Name: (R_S)-5-benzyloxy-5-hydroxymethyl-2-methoxy-2-(p-toluenesulfinyl-methyl)tetrahydropyran
• CAS No.: 204325-73-5
• Molecular Formula: C₂₂H₂₈O₅S
• Molecular Weight: 404.527

Synonyms:(R_S)-5-benzyloxy-5-hydroxymethyl-2-methoxy-2-(p-toluenesulfinyl-methyl)tetrahydropyran

Chemical Property of (R_S)-5-benzyloxy-5-hydroxymethyl-2-methoxy-2-(p-toluenesulfinyl-methyl)tetrahydropyran

Chemical Property:

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Technology Process of (R_S)-5-benzyloxy-5-hydroxymethyl-2-methoxy-2-(p-toluenesulfinyl-methyl)tetrahydropyran

There total 6 articles about (R_S)-5-benzyloxy-5-hydroxymethyl-2-methoxy-2-(p-toluenesulfinyl-methyl)tetrahydropyran 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: 90.0%

methanol (67-56-1) + 5-Benzyloxy-6-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-1-((R)-toluene-4-sulfinyl)-hexan-2-one (204325-72-4) → (RS)-5-benzyloxy-5-hydroxymethyl-2-methoxy-2-(p-toluenesulfinyl-methyl)tetrahydropyran (204325-73-5)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; for 3h; Ambient temperature;

DOI:10.1248/cpb.46.217

Reference yield:

(R)-methyl p-tolyl sulfoxide (1519-39-7) → (RS)-5-benzyloxy-5-hydroxymethyl-2-methoxy-2-(p-toluenesulfinyl-methyl)tetrahydropyran (204325-73-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) LDA / 1.) THF, 0 deg C, 15 min, 2.) THF, -78 deg C, 30 min

2: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / Ambient temperature

3: 90 percent / p-TsOH*H₂O / methanol / 3 h / Ambient temperature

With Dess-Martin periodane; toluene-4-sulfonic acid; lithium diisopropyl amide; In methanol; dichloromethane;

DOI:10.1248/cpb.46.217

Reference yield:

1-(tetrahydropyran-2-yloxy)-2-(tetrahydropyran-2-yloxymethyl)-5-hexen-2-ol (204325-69-9) → (RS)-5-benzyloxy-5-hydroxymethyl-2-methoxy-2-(p-toluenesulfinyl-methyl)tetrahydropyran (204325-73-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaH, tetra-n-butylammonium iodide / 1.) DMF, RT, 10 min, 2.) DMF, RT, 5 h

2: 1.) OsO₄, 2.) NaIO₄ / 1.) ether, water, RT, 5 min, 2.) ether, water, RT, 3 h

3: 1.) LDA / 1.) THF, 0 deg C, 15 min, 2.) THF, -78 deg C, 30 min

4: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.75 h / Ambient temperature

5: 90 percent / p-TsOH*H₂O / methanol / 3 h / Ambient temperature

With sodium periodate; osmium(VIII) oxide; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; lithium diisopropyl amide; In methanol; dichloromethane;

DOI:10.1248/cpb.46.217

upstream raw materials:

methanol

5-Benzyloxy-6-(tetrahydro-pyran-2-yloxy)-5-(tetrahydro-pyran-2-yloxymethyl)-1-((R)-toluene-4-sulfinyl)-hexan-2-one

(R)-methyl p-tolyl sulfoxide

1-(tetrahydropyran-2-yloxy)-2-(tetrahydropyran-2-yloxymethyl)-5-hexen-2-ol

Downstream raw materials:

(1S,5R)-5-methyl-1-para-toluenesulfonyloxymethyl-6,8-dioxabicyclo[3.2.1]octane

Toluene-4-sulfonic acid (S)-2-benzyloxy-2-hydroxymethyl-6-oxo-heptyl ester

Toluene-4-sulfonic acid (S)-3-benzyloxy-6-((R)-toluene-4-sulfinylmethyl)-3,4-dihydro-2H-pyran-3-ylmethyl ester

((R)-Toluene-4-sulfinyl)-acetic acid (S)-2-benzyloxy-4-oxo-2-(toluene-4-sulfonyloxymethyl)-butyl ester

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