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

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Chemical Name:2-[(2S,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-ethanol
CAS No.:808109-88-8
Molecular Formula:C₄₀H₆₀O₇Si₂
Molecular Weight:709.083
Hs Code.:

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

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

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

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

There total 15 articles about 2-[(2S,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxy-3-(4-methoxy-benzyloxy)-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: 60.0%

: 808109-87-7
(2S,3R,4R,5S,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxy-5-(4-methoxy-benzyloxy)-6-vinyl-tetrahydro-pyran

: 808109-88-8
2-[(2S,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-ethanol

Guidance literature:: (2S,3R,4R,5S,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxy-5-(4-methoxy-benzyloxy)-6-vinyl-tetrahydro-pyran; With borane-THF; In tetrahydrofuran; at 0 ℃;

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

: 808109-88-8
2-[(2S,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-ethanol

Guidance literature:: Multi-step reaction with 15 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: Bu₂SnO / toluene / Heating

4.2: 70 percent / KF / dimethylformamide

5.1: imidazole / dimethylformamide / 20 °C

6.1: DIBAL-H / CH₂Cl₂; toluene / -40 - -5 °C

7.1: pyridine / CH₂Cl₂ / 0 - 20 °C

8.1: aq. OsO₄; NMO / acetone / 20 °C

9.1: aq. NaIO₄ / methanol / 20 °C

10.1: NaBH₄ / methanol; diethyl ether / 0 °C

11.1: imidazole / dimethylformamide / 20 °C

12.1: LAH / diethyl ether / 0 °C

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

14.1: n-BuLi; DMSO / tetrahydrofuran / 0 - 20 °C

15.1: BH₃*THF / tetrahydrofuran / 0 °C

15.2: 60 percent / aq. NaBO₃ / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; borane-THF; oxalyl dichloride; boron trifluoride diethyl etherate; sodium methylate; diisobutylaluminium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
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

: 808109-88-8
2-[(2S,3S,4R,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-yl]-ethanol

Guidance literature:: Multi-step reaction with 13 steps

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

2.1: Bu₂SnO / toluene / Heating

2.2: 70 percent / KF / dimethylformamide

3.1: imidazole / dimethylformamide / 20 °C

4.1: DIBAL-H / CH₂Cl₂; toluene / -40 - -5 °C

5.1: pyridine / CH₂Cl₂ / 0 - 20 °C

6.1: aq. OsO₄; NMO / acetone / 20 °C

7.1: aq. NaIO₄ / methanol / 20 °C

8.1: NaBH₄ / methanol; diethyl ether / 0 °C

9.1: imidazole / dimethylformamide / 20 °C

10.1: LAH / diethyl ether / 0 °C

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

12.1: n-BuLi; DMSO / tetrahydrofuran / 0 - 20 °C

13.1: BH₃*THF / tetrahydrofuran / 0 °C

13.2: 60 percent / aq. NaBO₃ / 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; N-methyl-2-indolinone; borane-THF; oxalyl dichloride; diisobutylaluminium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;
DOI:10.1016/j.bmcl.2004.08.068