2,2-Dimethyl-propionic acid (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-ylmethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (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-ylmethyl ester
• CAS No.: 808109-47-9
• Molecular Formula: C₄₄H₆₆O₈Si₂
• Molecular Weight: 779.174

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid (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-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (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-ylmethyl ester

There total 11 articles about 2,2-Dimethyl-propionic acid (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-ylmethyl ester 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:

tert-butylchlorodiphenylsilane (58479-61-1) + 2,2-Dimethyl-propionic acid (2S,3S,4R,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-6-(2-hydroxy-ethyl)-4-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-ylmethyl ester → 2,2-Dimethyl-propionic acid (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-ylmethyl ester (808109-47-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.bmcl.2004.08.068

Reference yield:

α/β‐L‐glucopyranosyl‐1,2,3,4,5‐pentaacetate (188783-40-6) → 2,2-Dimethyl-propionic acid (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-ylmethyl ester (808109-47-9)

Guidance literature:

Multi-step reaction with 11 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

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; boron trifluoride diethyl etherate; sodium methylate; diisobutylaluminium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;

DOI:10.1016/j.bmcl.2004.08.068

Reference yield:

(2S,3S,4S,5R,6S)-2-Allyl-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (477845-03-7) → 2,2-Dimethyl-propionic acid (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-ylmethyl ester (808109-47-9)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; 1H-imidazole; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; diisobutylaluminium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/j.bmcl.2004.08.068

upstream raw materials:

tert-butylchlorodiphenylsilane

α/β‐L‐glucopyranosyl‐1,2,3,4,5‐pentaacetate

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

(4aS,6S,7S,8S,8aR)-6-Allyl-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol

Downstream raw materials:

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

[(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]-acetaldehyde

(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

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