(3R,R_S)-3-benzyloxy-3,4-dihydro-3-hydroxymethyl-6-(p-toluenesulfinylmethyl)-2H-pyran

Base Information

• Chemical Name: (3R,R_S)-3-benzyloxy-3,4-dihydro-3-hydroxymethyl-6-(p-toluenesulfinylmethyl)-2H-pyran
• CAS No.: 204325-75-7
• Molecular Formula: C₂₁H₂₄O₄S
• Molecular Weight: 372.485

Synonyms:(3R,R_S)-3-benzyloxy-3,4-dihydro-3-hydroxymethyl-6-(p-toluenesulfinylmethyl)-2H-pyran

Chemical Property of (3R,R_S)-3-benzyloxy-3,4-dihydro-3-hydroxymethyl-6-(p-toluenesulfinylmethyl)-2H-pyran

Chemical Property:

Purity/Quality:

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Technology Process of (3R,R_S)-3-benzyloxy-3,4-dihydro-3-hydroxymethyl-6-(p-toluenesulfinylmethyl)-2H-pyran

There total 8 articles about (3R,R_S)-3-benzyloxy-3,4-dihydro-3-hydroxymethyl-6-(p-toluenesulfinylmethyl)-2H-pyran 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: 21.0%

(RS)-4-benzyloxy-1-(p-toluenesulfinylmethyl)-2,6-dioxabicyclo[2.2.2]octane → (3R,RS)-3-benzyloxy-3,4-dihydro-3-hydroxymethyl-6-(p-toluenesulfinylmethyl)-2H-pyran (204325-75-7) + (3S,RS)-3-benzyloxy-3,4-dihydro-3-hydroxymethyl-6-(p-toluenesulfinylmethyl)-2H-pyran

Guidance literature:

With 2,6-dimethylpyridine; titanium tetrachloride; In tetrahydrofuran; a) from -78 deg C to 5 deg C, 5 h, b) 5 deg C, 15 h;

DOI:10.1248/cpb.46.217

Reference yield:

(R)-methyl p-tolyl sulfoxide (1519-39-7) → (3R,RS)-3-benzyloxy-3,4-dihydro-3-hydroxymethyl-6-(p-toluenesulfinylmethyl)-2H-pyran (204325-75-7)

Guidance literature:

Multi-step reaction with 5 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

4: 75 percent / ZnCl₂ / CH₂Cl₂ / 10 h / Ambient temperature

5: 52 percent / 2,6-lutidine, TiCl₄ / tetrahydrofuran / a) from -78 deg C to 5 deg C, 5 h, b) 5 deg C, 15 h

With 2,6-dimethylpyridine; titanium tetrachloride; Dess-Martin periodane; toluene-4-sulfonic acid; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; 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) → (3R,RS)-3-benzyloxy-3,4-dihydro-3-hydroxymethyl-6-(p-toluenesulfinylmethyl)-2H-pyran (204325-75-7)

Guidance literature:

Multi-step reaction with 7 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

6: 75 percent / ZnCl₂ / CH₂Cl₂ / 10 h / Ambient temperature

7: 52 percent / 2,6-lutidine, TiCl₄ / tetrahydrofuran / a) from -78 deg C to 5 deg C, 5 h, b) 5 deg C, 15 h

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; zinc(II) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1248/cpb.46.217

upstream raw materials:

(R)-methyl p-tolyl sulfoxide

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

2-benzyloxy-1-(tetrahydropyran-2-yloxy)-2-(tetrahydropyran-2-yloxymethyl)-5-hexene

2-benzyloxy-5-(tetrahydropyran-2-yloxy)-4-(tetrahydropyran-2-yloxymethyl)pentanale

Downstream raw materials:

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

(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

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

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