ethyl [(2S,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]acetate

Base Information

Chemical Name:ethyl [(2S,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]acetate
CAS No.:635727-12-7
Molecular Formula:C₂₇H₄₆O₅Si
Molecular Weight:478.745
Hs Code.:

Synonyms:ethyl [(2S,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]acetate

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Chemical Property of ethyl [(2S,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]acetate

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Technology Process of ethyl [(2S,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]acetate

There total 9 articles about ethyl [(2S,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]acetate 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: 81.0%

: 635727-11-6
ethyl (5R,6R,7R)-8-benzyloxy-7-hydroxy-6-methyl-5-triisopropylsilanyloxy-(2E)-octenoate

: 635727-12-7
ethyl [(2S,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]acetate

Guidance literature:: With sodium hydride; In tetrahydrofuran; at -78 - -20 ℃;
DOI:10.1002/anie.200352016

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 635727-12-7
ethyl [(2S,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]acetate

Guidance literature:: Multi-step reaction with 3 steps

1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

2: 87 percent / aq. DDQ / CH₂Cl₂ / 3 h / 20 °C

3: 81 percent / NaH / tetrahydrofuran / 3.5 h / -78 - -20 °C

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

Reference yield:

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

: 635727-12-7
ethyl [(2S,4R,5R,6R)-6-benzyloxymethyl-5-methyl-4-triisopropylsilanyloxytetrahydropyran-2-yl]acetate

Guidance literature:: Multi-step reaction with 8 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

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