2-[(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-ethanol

Base Information

Chemical Name:2-[(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-ethanol
CAS No.:808109-81-1
Molecular Formula:C₄₀H₆₀O₆Si₂
Molecular Weight:693.084
Hs Code.:

2-[(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-ethanol

Synonyms:2-[(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-ethanol

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Chemical Property of 2-[(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-ethanol

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Technology Process of 2-[(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-ethanol

There total 16 articles about 2-[(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-ethanol 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: 46.0%

: 808109-43-5
(2S,3S,4R,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-4-methyl-6-vinyl-tetrahydro-pyran

: 808109-81-1
2-[(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-ethanol

Guidance literature:: (2S,3S,4R,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-5-(4-methoxy-benzyloxy)-4-methyl-6-vinyl-tetrahydro-pyran; With dimethylsulfide borane complex; In tetrahydrofuran; at -10 - 20 ℃;

With sodium perborate; at 20 ℃;
DOI:10.1016/j.bmcl.2004.08.068

Reference yield:

: 188783-40-6
α/β‐L‐glucopyranosyl‐1,2,3,4,5‐pentaacetate

: 808109-81-1
2-[(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-ethanol

Guidance literature:: Multi-step reaction with 16 steps

1.1: 67 percent / BF₃*Et₂O / acetonitrile / 80 °C

2.1: 84 percent / NaOMe / methanol / 20 °C

3.1: 90 percent / p-TsOH / dimethylformamide / 20 °C

4.1: 71 percent / pyridine / 20 °C

5.1: 79 percent / NaOMe / methanol / 20 °C

6.1: 75 percent / diethyl ether / Heating

7.1: 74 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8.1: 88 percent / LAH / diethyl ether / 0 °C

9.1: DIEA / CH₂Cl₂ / 0 °C

10.1: O₃ / CH₂Cl₂ / -78 °C

11.1: NaBH₄ / ethanol / 20 °C

12.1: 73 percent / imidazole; DMAP / dimethylformamide / 20 °C

13.1: 59 percent / DIBAL-H / CH₂Cl₂ / -78 °C

14.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

15.1: n-BuLi; DMSO / tetrahydrofuran

16.1: BH₃*DMS / tetrahydrofuran / -10 - 20 °C

16.2: 46 percent / aq. NaBO₃ / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; boron trifluoride diethyl etherate; sodium methylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 6.1: Grignard reaction;
DOI:10.1016/j.bmcl.2004.08.068

Reference yield:

: 477845-03-7
(2S,3S,4S,5R,6S)-2-Allyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

: 808109-81-1
2-[(2S,3R,4R,5S,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-3-(4-methoxy-benzyloxy)-4-methyl-tetrahydro-pyran-2-yl]-ethanol

Guidance literature:: Multi-step reaction with 14 steps

1.1: 90 percent / p-TsOH / dimethylformamide / 20 °C

2.1: 71 percent / pyridine / 20 °C

3.1: 79 percent / NaOMe / methanol / 20 °C

4.1: 75 percent / diethyl ether / Heating

5.1: 74 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: 88 percent / LAH / diethyl ether / 0 °C

7.1: DIEA / CH₂Cl₂ / 0 °C

8.1: O₃ / CH₂Cl₂ / -78 °C

9.1: NaBH₄ / ethanol / 20 °C

10.1: 73 percent / imidazole; DMAP / dimethylformamide / 20 °C

11.1: 59 percent / DIBAL-H / CH₂Cl₂ / -78 °C

12.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

13.1: n-BuLi; DMSO / tetrahydrofuran

14.1: BH₃*DMS / tetrahydrofuran / -10 - 20 °C

14.2: 46 percent / aq. NaBO₃ / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; sodium methylate; diisobutylaluminium hydride; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; 4.1: Grignard reaction;
DOI:10.1016/j.bmcl.2004.08.068