7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(4-methoxy-phenyl)-8-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

• Chemical Name: 7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(4-methoxy-phenyl)-8-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine
• CAS No.: 808109-42-4
• Molecular Formula: C₃₉H₅₆O₆Si₂
• Molecular Weight: 677.041

Synonyms:7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(4-methoxy-phenyl)-8-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property of 7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(4-methoxy-phenyl)-8-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(4-methoxy-phenyl)-8-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine

There total 13 articles about 7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(4-methoxy-phenyl)-8-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine 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: 73.0%

tert-butylchlorodiphenylsilane (58479-61-1) + 2-[(4aS,6S,7S,8R,8aR)-7-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-8-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol (808109-79-7) → 7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(4-methoxy-phenyl)-8-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine (808109-42-4)

Guidance literature:

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

DOI:10.1016/j.bmcl.2004.08.068

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → 7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(4-methoxy-phenyl)-8-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine (808109-42-4)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / p-TsOH / dimethylformamide / 20 °C

2: 71 percent / pyridine / 20 °C

3: 79 percent / NaOMe / methanol / 20 °C

4: 75 percent / diethyl ether / Heating

5: 74 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6: 88 percent / LAH / diethyl ether / 0 °C

7: DIEA / CH₂Cl₂ / 0 °C

8: O₃ / CH₂Cl₂ / -78 °C

9: NaBH₄ / ethanol / 20 °C

10: 73 percent / imidazole; DMAP / dimethylformamide / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; sodium methylate; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; 4: Grignard reaction;

DOI:10.1016/j.bmcl.2004.08.068

Reference yield:

α/β‐L‐glucopyranosyl‐1,2,3,4,5‐pentaacetate (188783-40-6) → 7-(tert-butyl-dimethyl-silanyloxy)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-(4-methoxy-phenyl)-8-methyl-hexahydro-pyrano[3,2-d][1,3]dioxine (808109-42-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 67 percent / BF₃*Et₂O / acetonitrile / 80 °C

2: 84 percent / NaOMe / methanol / 20 °C

3: 90 percent / p-TsOH / dimethylformamide / 20 °C

4: 71 percent / pyridine / 20 °C

5: 79 percent / NaOMe / methanol / 20 °C

6: 75 percent / diethyl ether / Heating

7: 74 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

8: 88 percent / LAH / diethyl ether / 0 °C

9: DIEA / CH₂Cl₂ / 0 °C

10: O₃ / CH₂Cl₂ / -78 °C

11: NaBH₄ / ethanol / 20 °C

12: 73 percent / imidazole; DMAP / dimethylformamide / 20 °C

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; boron trifluoride diethyl etherate; sodium methylate; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 6: Grignard reaction;

DOI:10.1016/j.bmcl.2004.08.068

upstream raw materials:

tert-butylchlorodiphenylsilane

2-[(4aS,6S,7S,8R,8aR)-7-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-8-methyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

p-Anisaldehyde dimethyl acetal

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

Downstream raw materials:

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

(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

[(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]-acetaldehyde

[(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]-methanol

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