(2S,3S,4R,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-[2-(4-methoxy-phenoxy)-ethyl]-3-propyl-tetrahydro-pyran-4-carbaldehyde

Base Information

• Chemical Name: (2S,3S,4R,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-[2-(4-methoxy-phenoxy)-ethyl]-3-propyl-tetrahydro-pyran-4-carbaldehyde
• CAS No.: 157117-03-8
• Molecular Formula: C₃₆H₄₈O₆Si
• Molecular Weight: 604.859

Synonyms:(2S,3S,4R,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-[2-(4-methoxy-phenoxy)-ethyl]-3-propyl-tetrahydro-pyran-4-carbaldehyde

Chemical Property of (2S,3S,4R,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-[2-(4-methoxy-phenoxy)-ethyl]-3-propyl-tetrahydro-pyran-4-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-[2-(4-methoxy-phenoxy)-ethyl]-3-propyl-tetrahydro-pyran-4-carbaldehyde

There total 13 articles about (2S,3S,4R,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-[2-(4-methoxy-phenoxy)-ethyl]-3-propyl-tetrahydro-pyran-4-carbaldehyde 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-Butyl-{(3R,4R,5S,7S,8R)-7-methoxy-8-[2-(4-methoxy-phenoxy)-ethyl]-4-propyl-1,6-dioxa-spiro[2.5]oct-5-ylmethoxy}-diphenyl-silane (157117-02-7) → (2S,3S,4R,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-[2-(4-methoxy-phenoxy)-ethyl]-3-propyl-tetrahydro-pyran-4-carbaldehyde (157117-03-8)

Guidance literature:

With methylaluminium bis(4-bromo-2,6-di-tert.-butylphenoxide); In dichloromethane; at -78 ℃;

DOI:10.1016/S0040-4039(00)75797-2

Reference yield:

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose (33208-47-8) → (2S,3S,4R,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-[2-(4-methoxy-phenoxy)-ethyl]-3-propyl-tetrahydro-pyran-4-carbaldehyde (157117-03-8)

Guidance literature:

Multi-step reaction with 14 steps

1: diethyl ether / Ambient temperature

2: Et₃N / DMAP / CH₂Cl₂ / Ambient temperature

4: DEAD-Ph₃P / CH₂Cl₂ / Ambient temperature

5: H₂ / Pd/C / methanol

6: Et₃N / CH₂Cl₂ / -10 °C

7: MeONa / methanol / Ambient temperature

8: diethyl ether / Ambient temperature

9: H₂ / Pd/C / methanol

10: H⁽¹⁺⁾

11: pyridine

12: Swern oxidation

13: MeLi / tetrahydrofuran / -78 °C

14: methylaluminum bis-(4-bromo-2,6-di-tert-butyl-phenoxide) (MABR) / CH₂Cl₂ / -78 °C

With pyridine; methyllithium; hydrogen; sodium methylate; hydrogen cation; methylaluminium bis(4-bromo-2,6-di-tert.-butylphenoxide); triethylamine; triphenylphosphine; diethylazodicarboxylate; dmap; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)75797-2

Reference yield:

1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(2-propenyl)-β-D-glucopyranose (104206-19-1) → (2S,3S,4R,5R,6S)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-[2-(4-methoxy-phenoxy)-ethyl]-3-propyl-tetrahydro-pyran-4-carbaldehyde (157117-03-8)

Guidance literature:

Multi-step reaction with 13 steps

1: Et₃N / DMAP / CH₂Cl₂ / Ambient temperature

3: DEAD-Ph₃P / CH₂Cl₂ / Ambient temperature

4: H₂ / Pd/C / methanol

5: Et₃N / CH₂Cl₂ / -10 °C

6: MeONa / methanol / Ambient temperature

7: diethyl ether / Ambient temperature

8: H₂ / Pd/C / methanol

9: H⁽¹⁺⁾

10: pyridine

11: Swern oxidation

12: MeLi / tetrahydrofuran / -78 °C

13: methylaluminum bis-(4-bromo-2,6-di-tert-butyl-phenoxide) (MABR) / CH₂Cl₂ / -78 °C

With pyridine; methyllithium; hydrogen; sodium methylate; hydrogen cation; methylaluminium bis(4-bromo-2,6-di-tert.-butylphenoxide); triethylamine; triphenylphosphine; diethylazodicarboxylate; dmap; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(00)75797-2

upstream raw materials:

tert-Butyl-{(3R,4R,5S,7S,8R)-7-methoxy-8-[2-(4-methoxy-phenoxy)-ethyl]-4-propyl-1,6-dioxa-spiro[2.5]oct-5-ylmethoxy}-diphenyl-silane

4-O-benzyl-1,6:2,3-dianhydro-β-D-mannopyranose

1,6-anhydro-4-O-benzyl-2-deoxy-2-C-(2-propenyl)-β-D-glucopyranose

(1R,2R,4R,5R,6R)-5-[2-(4-Methoxy-phenoxy)-ethyl]-3,7,9-trioxa-tricyclo[4.2.1.0^2,4]nonane

Downstream raw materials:

2,2-Dimethyl-butyric acid (1S,2S,3S,6R)-2-[2-(4-methoxy-phenoxy)-ethyl]-3-methyl-6-propyl-cyclohexylmethyl ester

2,2-Dimethyl-butyric acid (2S,3R,4S,5S)-2-methoxy-3-[2-(4-methoxy-phenoxy)-ethyl]-6-methylene-5-propyl-tetrahydro-pyran-4-ylmethyl ester

2,2-Dimethyl-butyric acid (2S,3R,4S,5S,6S)-2-methoxy-3-[2-(4-methoxy-phenoxy)-ethyl]-6-(2-nitro-phenylselanylmethyl)-5-propyl-tetrahydro-pyran-4-ylmethyl ester

2,2-Dimethyl-butyric acid (2S,3S,4S,5R,6S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-5-[2-(4-methoxy-phenoxy)-ethyl]-3-propyl-tetrahydro-pyran-4-ylmethyl ester

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