methyl [(2S,3S,4S,6R)-6-(2-hydroxyeth-1-yl)-3-methyl-4-[(triisopropylsilyl)oxy]-oxan-2-yl]acetate

Base Information

Chemical Name:methyl [(2S,3S,4S,6R)-6-(2-hydroxyeth-1-yl)-3-methyl-4-[(triisopropylsilyl)oxy]-oxan-2-yl]acetate
CAS No.:366454-74-2
Molecular Formula:C₂₀H₄₀O₅Si
Molecular Weight:388.62
Hs Code.:

Synonyms:methyl [(2S,3S,4S,6R)-6-(2-hydroxyeth-1-yl)-3-methyl-4-[(triisopropylsilyl)oxy]-oxan-2-yl]acetate

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Chemical Property of methyl [(2S,3S,4S,6R)-6-(2-hydroxyeth-1-yl)-3-methyl-4-[(triisopropylsilyl)oxy]-oxan-2-yl]acetate

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Technology Process of methyl [(2S,3S,4S,6R)-6-(2-hydroxyeth-1-yl)-3-methyl-4-[(triisopropylsilyl)oxy]-oxan-2-yl]acetate

There total 1 articles about methyl [(2S,3S,4S,6R)-6-(2-hydroxyeth-1-yl)-3-methyl-4-[(triisopropylsilyl)oxy]-oxan-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:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 366454-74-2
methyl [(2S,3S,4S,6R)-6-(2-hydroxyeth-1-yl)-3-methyl-4-[(triisopropylsilyl)oxy]-oxan-2-yl]acetate

Guidance literature:: Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 18 h / 20 °C

2: hydrogen / Pd/C / ethanol / 15 h / 20 °C

With 1H-imidazole; hydrogen; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;
DOI:10.1021/ol050840o

Reference yield:

: 366454-74-2
methyl [(2S,3S,4S,6R)-6-(2-hydroxyeth-1-yl)-3-methyl-4-[(triisopropylsilyl)oxy]-oxan-2-yl]acetate

: 215120-40-4
(1S,4R,5R,7R,9R,13S,14S,15S)-3,11-dioxo-4-hydroxy-9-[(E)-2-iodoethenyl]-15-[[3-O-(4-O-benzyl-2,3-di-O-methyl-α-L-fucopyranosyl)-2,4-di-O-methyl-β-D-xylopyranosyl]oxy]-5,8,8,14-tetramethyl-10,17,18-trioxatricyclo[11.3.1.1^4,7]actadecane

Guidance literature:: Multi-step reaction with 13 steps

1.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

2.1: 84 percent / K₂CO₃ / methanol / 2 h / 20 °C

3.1: 77 percent / 9-bromo-9-borobicyclo[3.3.1]nonane / CH₂Cl₂ / 3 h / 20 °C

4.1: CrCl₂; NiCl₂ / dimethylformamide / 72 h

5.1: PPTS / methanol / 35 °C

5.2: 87 percent / aq. NaOH / methanol / 20 °C

6.1: 2,4,6-Cl₃C₆H₂COCl; Et₃N / tetrahydrofuran / 20 °C

6.2: 46 percent / DMAP / tetrahydrofuran; toluene / Heating

7.1: 70 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

8.1: O₃ / CH₂Cl₂; methanol / -78 °C

8.2: 55 percent / Ph₃P / CH₂Cl₂; methanol / 20 °C

9.1: 71 percent / CrCl₂ / tetrahydrofuran / 20 °C

10.1: 97 percent / PPTS / methanol; CH₂Cl₂ / 20 °C

11.1: Dess-Martin periodinane / pyridine; CH₂Cl₂ / 0 °C

12.1: 1.5 mg / HF*pyridine / tetrahydrofuran; CH₂Cl₂ / 16 h

13.1: NBS; 4 Angstroem molecular sieves / acetonitrile / 0.83 h / -35 - 20 °C

With 2,6-dimethylpyridine; B-Br-9-BBN; chromium dichloride; N-Bromosuccinimide; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; ozone; triethylamine; nickel dichloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Dess-Martin oxidation / 9.1: Takai reaction / 11.1: Dess-Martin oxidation;
DOI:10.1021/ja011256n

Reference yield:

: 366454-74-2
methyl [(2S,3S,4S,6R)-6-(2-hydroxyeth-1-yl)-3-methyl-4-[(triisopropylsilyl)oxy]-oxan-2-yl]acetate

: 15-[4-(5-benzyloxy-3,4-dimethoxy-6-methyl-tetrahydro-pyran-2-yloxy)-3,5-dimethoxy-tetrahydro-pyran-2-yloxy]-4-hydroxy-9-(2-iodo-vinyl)-5,8,8,14-tetramethyl-10,17,18-trioxa-tricyclo[11.3.1.1^4,7]octadecane-3,11-dione

Guidance literature:: Multi-step reaction with 12 steps

1.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

2.1: 84 percent / K₂CO₃ / methanol / 2 h / 20 °C

3.1: 9-bromo-9-borabicyclo[3.3.1]nonane / CH₂Cl₂ / 3 h / 20 °C

4.1: CrCl₂; NiCl₂ / dimethylformamide / 72 h

5.1: 87 percent / PPTS / methanol / 19 h / 35 °C

6.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1.5 h

6.2: 46 percent / DMAP / tetrahydrofuran; toluene / 0.25 h / Heating

7.1: 70 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

8.1: O₃ / CH₂Cl₂; methanol / 0.75 h / -78 °C

8.2: 81 percent / Ph₃P / CH₂Cl₂; methanol / 4.5 h / -78 - 20 °C

9.1: 71 percent / CrCl₂ / tetrahydrofuran / 4.5 h / 20 °C

10.1: 97 percent / PPTS / methanol; CH₂Cl₂ / 5.5 h / 20 °C

11.1: Dess-Martin periodinane / dimethylsulfoxide / 1.5 h / 0 °C

11.2: 87 percent / HF*pyridine / tetrahydrofuran; pyridine / 16 h

12.1: 27 percent / 4 Angstroem molecular sieves; N-bromosuccinimide / acetonitrile / 0.83 h / -35 - 20 °C

With 2,6-dimethylpyridine; B-Br-9-BBN; chromium dichloride; N-Bromosuccinimide; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; pyridinium p-toluenesulfonate; potassium carbonate; Dess-Martin periodane; ozone; triethylamine; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 4.1: Nozaki-Hiyama-Kishi reaction / 6.2: Yamaguchi lactonization / 9.1: Takai reaction;
DOI:10.1021/jo0503862