{6-[4-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enyl]-5-methoxy-5,6-dihydro-2H-pyran-2-yl}-acetaldehyde

Base Information

• Chemical Name: {6-[4-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enyl]-5-methoxy-5,6-dihydro-2H-pyran-2-yl}-acetaldehyde
• CAS No.: 847834-97-3
• Molecular Formula: C₃₀H₄₀O₄Si
• Molecular Weight: 492.731

Synonyms:{6-[4-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enyl]-5-methoxy-5,6-dihydro-2H-pyran-2-yl}-acetaldehyde

Chemical Property of {6-[4-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enyl]-5-methoxy-5,6-dihydro-2H-pyran-2-yl}-acetaldehyde

Chemical Property:

Purity/Quality:

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Technology Process of {6-[4-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enyl]-5-methoxy-5,6-dihydro-2H-pyran-2-yl}-acetaldehyde

There total 15 articles about {6-[4-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enyl]-5-methoxy-5,6-dihydro-2H-pyran-2-yl}-acetaldehyde 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: 50.0%

tert-butyl-[5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methylene-pentyloxy]-diphenyl-silane (847835-12-5) → {6-[4-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enyl]-5-methoxy-5,6-dihydro-2H-pyran-2-yl}-acetaldehyde (847834-97-3)

Guidance literature:

With acetic acid; at 60 ℃;

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) → {6-[4-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enyl]-5-methoxy-5,6-dihydro-2H-pyran-2-yl}-acetaldehyde (847834-97-3)

Guidance literature:

Multi-step reaction with 14 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

11: 80 percent / TPAP; NMO / CH₂Cl₂

12: 65 percent / [(Ph₃P)CuH]6 / toluene; H₂O

13: 90 percent / n-BuLi / tetrahydrofuran / 0 °C

14: 50 percent / aq. HOAc / 60 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; N-iodo-succinimide; n-butyllithium; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; tetrapropylammonium perruthennate; (triphenylphosphine)copper(I) hydride hexamer; tetrabutyl ammonium fluoride; sodium hydride; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; silver nitrate; acetic acid; chromium dichloride; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; benzene; 12: double Stryker-type reduction;

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) → {6-[4-(tert-butyl-diphenyl-silanyloxymethyl)-pent-4-enyl]-5-methoxy-5,6-dihydro-2H-pyran-2-yl}-acetaldehyde (847834-97-3)

Guidance literature:

Multi-step reaction with 15 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

12: 80 percent / TPAP; NMO / CH₂Cl₂

13: 65 percent / [(Ph₃P)CuH]6 / toluene; H₂O

14: 90 percent / n-BuLi / tetrahydrofuran / 0 °C

15: 50 percent / aq. HOAc / 60 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium periodate; N-iodo-succinimide; n-butyllithium; N-methyl-2-indolinone; 2,6-di-tert-butyl-pyridine; tetrapropylammonium perruthennate; (triphenylphosphine)copper(I) hydride hexamer; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; silver nitrate; acetic acid; chromium dichloride; nickel dichloride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; benzene; 13: double Stryker-type reduction;

DOI:10.1016/j.tetlet.2004.12.056

upstream raw materials:

tert-butyl-[5-(6-[1,3]dioxolan-2-ylmethyl-3-methoxy-3,6-dihydro-2H-pyran-2-yl)-2-methylene-pentyloxy]-diphenyl-silane

(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

D-glucal triacetate

Downstream raw materials:

tert-butyl-[5-(3-methoxy-6-prop-2-ynyl-3,6-dihydro-2H-pyran-2-yl)-2-methylene-pentyloxy]-diphenyl-silane

tert-butyl-{5-[6-(3,3-dibromo-allyl)-3-methoxy-3,6-dihydro-2H-pyran-2-yl]-2-methylene-pentyloxy}-diphenyl-silane

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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