(2S,3R,4R,6R)-2-Benzyloxymethyl-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-ol

Base Information

• Chemical Name: (2S,3R,4R,6R)-2-Benzyloxymethyl-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-ol
• CAS No.: 819066-87-0
• Molecular Formula: C₃₂H₄₂O₅Si
• Molecular Weight: 534.768

Synonyms:(2S,3R,4R,6R)-2-Benzyloxymethyl-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-ol

Chemical Property of (2S,3R,4R,6R)-2-Benzyloxymethyl-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,6R)-2-Benzyloxymethyl-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-ol

There total 13 articles about (2S,3R,4R,6R)-2-Benzyloxymethyl-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-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:

(3aS,4S,6R,7aR)-4-Benzyloxymethyl-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2,3a-trimethyl-hexahydro-1,5-dioxa-2-sila-indene (819066-86-9) → (2S,3R,4R,6R)-2-Benzyloxymethyl-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-ol (819066-87-0)

Guidance literature:

With dihydrogen peroxide; potassium hydrogencarbonate; In tetrahydrofuran; methanol; at 90 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2004.10.071

Reference yield:

(3S,4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methyl-tetrahydro-pyran-2-one (132958-25-9) → (2S,3R,4R,6R)-2-Benzyloxymethyl-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-ol (819066-87-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 97 percent / 2,6-lutidine / dimethylformamide / 13 h / 20 °C

2: 97 percent / n-BuLi / tetrahydrofuran / 2 h / -78 °C

3: 51 percent / POCl₃ / pyridine / 48 h / 20 °C

4: n-Bu₄NF / tetrahydrofuran / 1 h / 20 °C

5: imidazole; 4-DMAP / CH₂Cl₂ / 2 h / 20 °C

6: 86 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 1 h / 20 °C

7: n-Bu₃SnCl; NaBH₃(CN); AIBN / 2-methyl-propan-2-ol / 3 h / 100 °C

8: KHCO₃; H₂O₂ / tetrahydrofuran; methanol / 1.5 h / 90 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); tributyltin chloride; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium cyanoborohydride; potassium hydrogencarbonate; triethylamine; trichlorophosphate; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 8: Tamao oxidation reaction;

DOI:10.1016/j.tetlet.2004.10.071

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → (2S,3R,4R,6R)-2-Benzyloxymethyl-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-3-methyl-tetrahydro-pyran-4-ol (819066-87-0)

Guidance literature:

Multi-step reaction with 4 steps

1: imidazole; 4-DMAP / CH₂Cl₂ / 2 h / 20 °C

2: 86 percent / Et₃N; 4-DMAP / CH₂Cl₂ / 1 h / 20 °C

3: n-Bu₃SnCl; NaBH₃(CN); AIBN / 2-methyl-propan-2-ol / 3 h / 100 °C

4: KHCO₃; H₂O₂ / tetrahydrofuran; methanol / 1.5 h / 90 °C

With 1H-imidazole; dmap; 2,2'-azobis(isobutyronitrile); tributyltin chloride; dihydrogen peroxide; sodium cyanoborohydride; potassium hydrogencarbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; tert-butyl alcohol; 4: Tamao oxidation reaction;

DOI:10.1016/j.tetlet.2004.10.071

upstream raw materials:

(3aS,4S,6R,7aR)-4-Benzyloxymethyl-6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2,3a-trimethyl-hexahydro-1,5-dioxa-2-sila-indene

(3S,4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-4-hydroxy-3-methyl-tetrahydro-pyran-2-one

tert-butylchlorodiphenylsilane

(S)-4-Benzyl-3-[(2S,3R)-4-((S)-2,2-diethyl-[1,3]dioxolan-4-yl)-3-hydroxy-2-methyl-butyryl]-oxazolidin-2-one

Downstream raw materials:

((4aR,5S,7R,8aR)-5-Benzyloxymethyl-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-7-ylmethoxy)-tert-butyl-diphenyl-silane

[(4aR,5R,7R,8aR)-7-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-5-yl]-methanol

[(4aR,5S,7R,8aR)-7-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxin-5-yl]-methanol

(4aR,5R,7R,8aR)-7-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2,4a-trimethyl-tetrahydro-pyrano[4,3-d][1,3]dioxine-5-carbaldehyde

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