4-[(2R,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]-(2E)-buten-1-ol

Base Information

Chemical Name:4-[(2R,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]-(2E)-buten-1-ol
CAS No.:635727-31-0
Molecular Formula:C₂₇H₄₆O₄Si
Molecular Weight:462.745
Hs Code.:

Synonyms:4-[(2R,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]-(2E)-buten-1-ol

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Chemical Property of 4-[(2R,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]-(2E)-buten-1-ol

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Technology Process of 4-[(2R,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]-(2E)-buten-1-ol

There total 12 articles about 4-[(2R,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]-(2E)-buten-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: 91.0%

: 635727-30-9
(E)-4-((2R,4R,5R,6R)-6-Benzyloxymethyl-5-methyl-4-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-but-2-enoic acid ethyl ester

: 635727-31-0
4-[(2R,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]-(2E)-buten-1-ol

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃;
DOI:10.1002/anie.200352016

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 635727-31-0
4-[(2R,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]-(2E)-buten-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

2.1: 87 percent / aq. DDQ / CH₂Cl₂ / 3 h / 20 °C

3.1: 81 percent / NaH / tetrahydrofuran / 3.5 h / -78 - -20 °C

4.1: DIBAL / toluene; CH₂Cl₂ / 0.17 h / -78 °C

5.1: NaH / tetrahydrofuran / 0.17 h / -78 °C

5.2: 826 mg / tetrahydrofuran / 0.33 h / -78 °C

6.1: 91 percent / DIBAL / CH₂Cl₂; toluene / 0.17 h / -78 °C

With 2,6-dimethylpyridine; sodium hydride; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; toluene; 5.2: Horner-Emmons olefination;
DOI:10.1055/s-2004-822340

Reference yield:

: 635727-09-2
(2R,3S)-1-Benzyloxy-3-methyl-pent-4-en-2-ol

: 635727-31-0
4-[(2R,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]-(2E)-buten-1-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: 97 percent / NaH; n-Bu₄NI / tetrahydrofuran / 9 h / 20 °C

2.1: aq. NaIO₄; OsO₄ / tetrahydrofuran / 4 h / 20 °C

3.1: diethyl ether / 5 h / -78 °C

3.2: 1.7 g / aq. NaOH; H₂O₂ / 6 h

4.1: aq. NaIO₄; OsO₄ / tetrahydrofuran / 6 h / 20 °C

5.1: 812 mg / benzene / 3 h / 80 - 90 °C

6.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

7.1: 87 percent / aq. DDQ / CH₂Cl₂ / 3 h / 20 °C

8.1: 81 percent / NaH / tetrahydrofuran / 3.5 h / -78 - -20 °C

9.1: DIBAL / toluene; CH₂Cl₂ / 0.17 h / -78 °C

10.1: NaH / tetrahydrofuran / 0.17 h / -78 °C

10.2: 826 mg / tetrahydrofuran / 0.33 h / -78 °C

11.1: 91 percent / DIBAL / CH₂Cl₂; toluene / 0.17 h / -78 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; benzene; 5.1: Wittig reaction / 10.2: Horner-Emmons olefination;
DOI:10.1055/s-2004-822340