(R_S)-5-benzyloxy-6-(tetrahydropyran-2-yloxy)-5-(tetrahydropyran-2-yloxymethyl)-1-(p-toluenesulfinyl)hexan-2-ol

Base Information

• Chemical Name: (R_S)-5-benzyloxy-6-(tetrahydropyran-2-yloxy)-5-(tetrahydropyran-2-yloxymethyl)-1-(p-toluenesulfinyl)hexan-2-ol
• CAS No.: 204589-34-4
• Molecular Formula: C₃₁H₄₄O₇S
• Molecular Weight: 560.752

Synonyms:(R_S)-5-benzyloxy-6-(tetrahydropyran-2-yloxy)-5-(tetrahydropyran-2-yloxymethyl)-1-(p-toluenesulfinyl)hexan-2-ol

Chemical Property of (R_S)-5-benzyloxy-6-(tetrahydropyran-2-yloxy)-5-(tetrahydropyran-2-yloxymethyl)-1-(p-toluenesulfinyl)hexan-2-ol

Chemical Property:

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Technology Process of (R_S)-5-benzyloxy-6-(tetrahydropyran-2-yloxy)-5-(tetrahydropyran-2-yloxymethyl)-1-(p-toluenesulfinyl)hexan-2-ol

There total 4 articles about (R_S)-5-benzyloxy-6-(tetrahydropyran-2-yloxy)-5-(tetrahydropyran-2-yloxymethyl)-1-(p-toluenesulfinyl)hexan-2-ol 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:

1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-2-propanone (32888-40-7) → (RS)-5-benzyloxy-6-(tetrahydropyran-2-yloxy)-5-(tetrahydropyran-2-yloxymethyl)-1-(p-toluenesulfinyl)hexan-2-ol (204589-34-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / diethyl ether / 2.5 h / 0 °C

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

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

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

With sodium periodate; osmium(VIII) oxide; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium diisopropyl amide; In diethyl ether;

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-6-(tetrahydropyran-2-yloxy)-5-(tetrahydropyran-2-yloxymethyl)-1-(p-toluenesulfinyl)hexan-2-ol (204589-34-4)

Guidance literature:

Multi-step reaction with 3 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

With sodium periodate; osmium(VIII) oxide; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium diisopropyl amide;

DOI:10.1248/cpb.46.217

Reference yield:

2-benzyloxy-1-(tetrahydropyran-2-yloxy)-2-(tetrahydropyran-2-yloxymethyl)-5-hexene (204325-70-2) → (RS)-5-benzyloxy-6-(tetrahydropyran-2-yloxy)-5-(tetrahydropyran-2-yloxymethyl)-1-(p-toluenesulfinyl)hexan-2-ol (204589-34-4)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium periodate; osmium(VIII) oxide; lithium diisopropyl amide;

DOI:10.1248/cpb.46.217

upstream raw materials:

(R)-methyl p-tolyl sulfoxide

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

1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-2-propanone

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

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

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

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