(2R,4S,5S,6R)-6-(5,5-Dimethyl-[1,3]dioxan-2-ylmethyl)-4-(4-methoxy-benzyloxy)-5-methyl-5-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-carbaldehyde

Base Information

• Chemical Name: (2R,4S,5S,6R)-6-(5,5-Dimethyl-[1,3]dioxan-2-ylmethyl)-4-(4-methoxy-benzyloxy)-5-methyl-5-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-carbaldehyde
• CAS No.: 1027042-05-2
• Molecular Formula: C₃₂H₅₄O₇Si
• Molecular Weight: 578.862

Synonyms:

Chemical Property of (2R,4S,5S,6R)-6-(5,5-Dimethyl-[1,3]dioxan-2-ylmethyl)-4-(4-methoxy-benzyloxy)-5-methyl-5-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2R,4S,5S,6R)-6-(5,5-Dimethyl-[1,3]dioxan-2-ylmethyl)-4-(4-methoxy-benzyloxy)-5-methyl-5-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-carbaldehyde

There total 12 articles about (2R,4S,5S,6R)-6-(5,5-Dimethyl-[1,3]dioxan-2-ylmethyl)-4-(4-methoxy-benzyloxy)-5-methyl-5-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-carbaldehyde 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:

[(2R,4S,5S,6R)-6-(5,5-Dimethyl-[1,3]dioxan-2-ylmethyl)-4-(4-methoxy-benzyloxy)-5-methyl-5-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl]-methanol (612846-87-4) → (2R,4S,5S,6R)-6-(5,5-Dimethyl-[1,3]dioxan-2-ylmethyl)-4-(4-methoxy-benzyloxy)-5-methyl-5-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-carbaldehyde (1027042-05-2)

Guidance literature:

With chromium(VI) oxide; In dimethyl sulfoxide;

DOI:10.1016/S0040-4039(03)01748-9

Reference yield:

sodium benzoate (532-32-1) → (2R,4S,5S,6R)-6-(5,5-Dimethyl-[1,3]dioxan-2-ylmethyl)-4-(4-methoxy-benzyloxy)-5-methyl-5-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-carbaldehyde (1027042-05-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: I₂; K₂CO₃ / acetonitrile / -25 - -15 °C

1.2: 1-methyl-pyrrolidin-2-one / 100 °C

2.1: OsO₄; NaIO₄ / methanol; H₂O; tetrahydrofuran / 0 °C

3.1: p-TsOH / toluene / 80 °C

4.1: K₂CO₃ / methanol / 20 °C

5.1: CrO₃ / dimethylsulfoxide

With chromium(VI) oxide; sodium periodate; osmium(VIII) oxide; iodine; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; dimethyl sulfoxide; toluene; acetonitrile; 3.1: Mitsunobu reaction / 5.1: Swern oxidation;

DOI:10.1016/S0040-4039(03)01748-9

Reference yield:

triisopropylsilyl chloride (13154-24-0) → (2R,4S,5S,6R)-6-(5,5-Dimethyl-[1,3]dioxan-2-ylmethyl)-4-(4-methoxy-benzyloxy)-5-methyl-5-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-carbaldehyde (1027042-05-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: DMAP; Et₃N / CH₂Cl₂ / 20 °C

2.1: I₂; K₂CO₃ / acetonitrile / -25 - -15 °C

2.2: 1-methyl-pyrrolidin-2-one / 100 °C

3.1: OsO₄; NaIO₄ / methanol; H₂O; tetrahydrofuran / 0 °C

4.1: p-TsOH / toluene / 80 °C

5.1: K₂CO₃ / methanol / 20 °C

6.1: CrO₃ / dimethylsulfoxide

With chromium(VI) oxide; dmap; sodium periodate; osmium(VIII) oxide; iodine; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide; toluene; acetonitrile; 4.1: Mitsunobu reaction / 6.1: Swern oxidation;

DOI:10.1016/S0040-4039(03)01748-9

upstream raw materials:

[(2R,4S,5S,6R)-6-(5,5-Dimethyl-[1,3]dioxan-2-ylmethyl)-4-(4-methoxy-benzyloxy)-5-methyl-5-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl]-methanol

sodium benzoate

triisopropylsilyl chloride

2,2-Dimethyl-1,3-propanediol

Downstream raw materials:

(E)-4-[(2R,4S,5S,6R)-6-(5,5-Dimethyl-[1,3]dioxan-2-ylmethyl)-4-(4-methoxy-benzyloxy)-5-methyl-5-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl]-but-3-en-1-ol

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