1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pent-3-yn-2-ol

Base Information

• Chemical Name: 1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pent-3-yn-2-ol
• CAS No.: 849361-69-9
• Molecular Formula: C₃₁H₄₀O₆Si
• Molecular Weight: 536.74

Synonyms:1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pent-3-yn-2-ol

Chemical Property of 1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pent-3-yn-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pent-3-yn-2-ol

There total 12 articles about 1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pent-3-yn-2-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:

(tert-butyldiphenylsilanyloxy)acetaldehyde (115869-43-7) + 6-[1,3]dioxolan-2-ylmethyl-2-(3-iodo-prop-2-ynyl)-3-methoxy-3,6-dihydro-2H-pyran (847834-95-1) → 1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pent-3-yn-2-ol (849361-69-9)

Guidance literature:

chromium dichloride; nickel dichloride; In tetrahydrofuran;

DOI:10.1016/j.tetlet.2004.12.056

Reference yield:

(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)acetaldehyde (136787-40-1) → 1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pent-3-yn-2-ol (849361-69-9)

Guidance literature:

Multi-step reaction with 10 steps

1: p-TsOH / benzene / Heating

2: K₂CO₃ / methanol

3: imidazole / dimethylformamide / 10 °C

4: NaH / dimethylformamide

5: 75 percent / TBAF / tetrahydrofuran

6: 2,6-di-t-butylpyridine / CH₂Cl₂ / -50 °C

7: 80 percent / HMPA / tetrahydrofuran / -78 °C

8: Cs₂CO₃ / methanol

9: 70 percent / AgNO₃; NIS / acetone

10: NiCl₂; CrCl₂ / tetrahydrofuran

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; N-iodo-succinimide; 2,6-di-tert-butyl-pyridine; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; silver nitrate; chromium dichloride; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/j.tetlet.2004.12.056

Reference yield:

acetic acid 3-acetoxy-6-(2,3-dihydroxy-propyl)-3,6-dihydro-2H-pyran-2-ylmethyl ester (849361-64-4) → 1-(tert-butyl-diphenyl-silanyloxy)-5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-pent-3-yn-2-ol (849361-69-9)

Guidance literature:

Multi-step reaction with 11 steps

1: NaIO₄; aq. NaHCO₃ / CH₂Cl₂

2: p-TsOH / benzene / Heating

3: K₂CO₃ / methanol

4: imidazole / dimethylformamide / 10 °C

5: NaH / dimethylformamide

6: 75 percent / TBAF / tetrahydrofuran

7: 2,6-di-t-butylpyridine / CH₂Cl₂ / -50 °C

8: 80 percent / HMPA / tetrahydrofuran / -78 °C

9: Cs₂CO₃ / methanol

10: 70 percent / AgNO₃; NIS / acetone

11: NiCl₂; CrCl₂ / tetrahydrofuran

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; N-iodo-succinimide; 2,6-di-tert-butyl-pyridine; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; silver nitrate; chromium dichloride; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1016/j.tetlet.2004.12.056

upstream raw materials:

(tert-butyldiphenylsilanyloxy)acetaldehyde

6-[1,3]dioxolan-2-ylmethyl-2-(3-iodo-prop-2-ynyl)-3-methoxy-3,6-dihydro-2H-pyran

(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)acetaldehyde

acetic acid 3-acetoxy-6-(2,3-dihydroxy-propyl)-3,6-dihydro-2H-pyran-2-ylmethyl ester

Downstream raw materials:

11-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-1-(3-methoxy-6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl)-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dien-6-ol

2-[6,11-bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-3-methoxy-6-prop-2-ynyl-3,6-dihydro-2H-pyran

4-{6-[6,11-bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-13-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5-methoxy-5,6-dihydro-2H-pyran-2-yl}-but-2-ynoic acid

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