(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

Base Information

• Chemical Name: (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
• CAS No.: 612846-89-6
• Molecular Formula: C₃₅H₆₀O₇Si
• Molecular Weight: 620.943

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 13 articles about (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 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-phenyl-5-(3-triethylsilanyloxy-propane-1-sulfonyl)-1H-tetrazole (612846-88-5) + (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) → (Z)-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 + (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 (612846-89-6)

Guidance literature:

1-phenyl-5-(3-triethylsilanyloxy-propane-1-sulfonyl)-1H-tetrazole; (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; With potassium hexamethylsilazane; In 1,2-dimethoxyethane; at -60 - 20 ℃;

With pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; at 0 ℃;

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

Reference yield:

sodium benzoate (532-32-1) → (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 (612846-89-6)

Guidance literature:

Multi-step reaction with 6 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

6.1: KHMDS / 1,2-dimethoxy-ethane / -60 - 20 °C

6.2: PPTS / tetrahydrofuran; methanol / 0 °C

With chromium(VI) oxide; sodium periodate; osmium(VIII) oxide; iodine; potassium hexamethylsilazane; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; 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) → (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 (612846-89-6)

Guidance literature:

Multi-step reaction with 7 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

7.1: KHMDS / 1,2-dimethoxy-ethane / -60 - 20 °C

7.2: PPTS / tetrahydrofuran; methanol / 0 °C

With chromium(VI) oxide; dmap; sodium periodate; osmium(VIII) oxide; iodine; potassium hexamethylsilazane; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; 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:

1-phenyl-5-(3-triethylsilanyloxy-propane-1-sulfonyl)-1H-tetrazole

(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

sodium benzoate

triisopropylsilyl chloride

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