(2R,3S,4aR,6S,8S,8aR)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-8-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-3-ol

Base Information

Chemical Name:(2R,3S,4aR,6S,8S,8aR)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-8-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-3-ol
CAS No.:155434-27-8
Molecular Formula:C₄₄H₇₆O₆Si₃
Molecular Weight:785.34
Hs Code.:

(2R,3S,4aR,6S,8S,8aR)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-8-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-3-ol

Synonyms:(2R,3S,4aR,6S,8S,8aR)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-8-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-3-ol

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Chemical Property of (2R,3S,4aR,6S,8S,8aR)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-8-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-3-ol

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Technology Process of (2R,3S,4aR,6S,8S,8aR)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-8-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-3-ol

There total 21 articles about (2R,3S,4aR,6S,8S,8aR)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-8-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-3-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: 98.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 155434-26-7
(2R,3S,4aR,6S,8S,8aR)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(3-hydroxy-propyl)-2-methyl-8-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-3-ol

: 155434-27-8
(2R,3S,4aR,6S,8S,8aR)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-8-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃;
DOI:10.1039/c39930001638

Reference yield:

: 122821-83-4
2,6-Anhydro-4-O-benzyl-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-D-altro-non-8-enitol

: 155434-27-8
(2R,3S,4aR,6S,8S,8aR)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-8-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: Multi-step reaction with 18 steps

1: 100 percent / imidazole / dimethylformamide / 3.5 h / Ambient temperature

2: 1.) O₃; 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C; 2.) CH₂Cl₂, -78 deg C to RT

3: benzene / 12 h / 80 °C

4: 95 percent / 1.0 M di-isobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

5: 93 percent / (+)-DET, Ti(O-iPr)2, 3.0 M t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 70 h / -20 °C

6: 100 percent / SO₃*py complex, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 3 h / Ambient temperature

7: 94 percent / 1.0 M NaHMDS / tetrahydrofuran / 1 h / 0 °C

8: 97 percent / 1.0 M TBAF / tetrahydrofuran / 0.25 h / 0 °C

9: 53 percent / camphorsulfonic acid / CH₂Cl₂ / 1 h / 0 °C

10: 97 percent / pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / 13 h / Ambient temperature

11: 1.) O₃; 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C; 2.) CH₂Cl₂, -78 deg C to RT

12: benzene / 6.5 h / 80 °C

13: 10 percent / H₂ / Pd(OH)2-C / methanol / 20 h / Ambient temperature

14: 82 percent / 1.0 M TBAF / tetrahydrofuran / 24 h / Ambient temperature

15: 91 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

16: 97 percent / 2,6-lutidine / dimethylformamide / 12 h / 70 °C

17: 94 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

18: 98 percent / imidazole / dimethylformamide / 3 h / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; diisobutylaluminum hydride; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; titanium(II) diisopropoxide; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; ozone; triethylamine; triphenylphosphine; palladium hydroxide - carbon; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

Reference yield:

: 155434-18-7
(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-((2S,3S)-3-methyl-3-vinyl-oxiranylmethyl)-tetrahydro-pyran-3-ol

: 155434-27-8
(2R,3S,4aR,6S,8S,8aR)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-propyl]-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-methyl-8-triisopropylsilanyloxy-octahydro-pyrano[3,2-b]pyran-3-ol

Guidance literature:: Multi-step reaction with 10 steps

1: 53 percent / camphorsulfonic acid / CH₂Cl₂ / 1 h / 0 °C

2: 97 percent / pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / 13 h / Ambient temperature

3: 1.) O₃; 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C; 2.) CH₂Cl₂, -78 deg C to RT

4: benzene / 6.5 h / 80 °C

5: 10 percent / H₂ / Pd(OH)2-C / methanol / 20 h / Ambient temperature

6: 82 percent / 1.0 M TBAF / tetrahydrofuran / 24 h / Ambient temperature

7: 91 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

8: 97 percent / 2,6-lutidine / dimethylformamide / 12 h / 70 °C

9: 94 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

10: 98 percent / imidazole / dimethylformamide / 3 h / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; ozone; triphenylphosphine; palladium hydroxide - carbon; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;