(R)-3-{(2S,3R,5S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-2-methyl-propionaldehyde

Base Information

• Chemical Name: (R)-3-{(2S,3R,5S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-2-methyl-propionaldehyde
• CAS No.: 83061-08-9
• Molecular Formula: C₂₈H₄₀O₄Si
• Molecular Weight: 468.709
• Mol file: 83061-08-9.mol

Synonyms:(R)-3-{(2S,3R,5S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-2-methyl-propionaldehyde

Chemical Property of (R)-3-{(2S,3R,5S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-2-methyl-propionaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-{(2S,3R,5S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-2-methyl-propionaldehyde

There total 7 articles about (R)-3-{(2S,3R,5S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-2-methyl-propionaldehyde 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: 95.0%

(R)-3-{(2S,3R,5S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-2-methyl-propan-1-ol (83060-93-9) → (R)-3-{(2S,3R,5S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-2-methyl-propionaldehyde (83061-08-9)

Guidance literature:

With dipyridine chromium trioxide; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ja00385a038

Reference yield:

(1S,2S,3R)-3-(2-Benzyloxy-ethyl)-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentanol (83061-03-4) → (R)-3-{(2S,3R,5S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-2-methyl-propionaldehyde (83061-08-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) CrO₃*2Py, 2.) MCPBA, NaHCO₃, <(Me)3CC₆H₂(Me)OH>2S / 1.) CH₂Cl₂, 0 deg C (10 min) -> 25 deg C (30 min), 2.) 0 deg C

2: LDA / tetrahydrofuran / -78 deg C -> -40 deg C

3: hydrogen / Pd-C / ethanol

4: CrO₃*2Py / CH₂Cl₂

5: TsOH

6: 95 percent / LiAlH₄ / diethyl ether / 0 °C

7: 95 percent / CrO₃*2Py / CH₂Cl₂ / 1 h / 0 °C

With lithium aluminium tetrahydride; <(Me)3CC6H2(Me)OH>2S; hydrogen; dipyridine chromium trioxide; sodium hydrogencarbonate; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/ja00385a038

Reference yield:

(5R,6S)-5-(2-Benzyloxy-ethyl)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-tetrahydro-pyran-2-one (83061-04-5) → (R)-3-{(2S,3R,5S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-2-methyl-propionaldehyde (83061-08-9)

Guidance literature:

Multi-step reaction with 6 steps

1: LDA / tetrahydrofuran / -78 deg C -> -40 deg C

2: hydrogen / Pd-C / ethanol

3: CrO₃*2Py / CH₂Cl₂

4: TsOH

5: 95 percent / LiAlH₄ / diethyl ether / 0 °C

6: 95 percent / CrO₃*2Py / CH₂Cl₂ / 1 h / 0 °C

With lithium aluminium tetrahydride; hydrogen; dipyridine chromium trioxide; toluene-4-sulfonic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/ja00385a038

upstream raw materials:

(R)-3-{(2S,3R,5S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-2-methyl-propan-1-ol

(1S,2S,3R)-3-(2-Benzyloxy-ethyl)-2-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-cyclopentanol

(R)-3-{(2S,3R,5S)-2-[(S)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-2-methyl-propionic acid methyl ester

(5R,6S)-5-(2-Benzyloxy-ethyl)-6-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-tetrahydro-pyran-2-one

Downstream raw materials:

(3R,4S)-4-[(2S,3R,5S)-3-((4E,6E)-(2R,3S,8R,9R)-3,9-Dihydroxy-2,6-dimethyl-8-trityloxymethyl-undeca-4,6-dienyl)-5-methoxy-tetrahydro-furan-2-yl]-3-hydroxy-pentanoic acid

(3R,4S)-4-[(2S,3R,5S)-3-((4E,6E)-(2R,3S,8R,9R)-3,9-Dihydroxy-2,6-dimethyl-8-trityloxymethyl-undeca-4,6-dienyl)-5-methoxy-tetrahydro-furan-2-yl]-3-hydroxy-pentanoic acid methyl ester

(7E,9E)-(2S,3aR,5R,6S,11R,12R,16R,17S,17aS)-12-Ethyl-6,16-dihydroxy-2-methoxy-5,9,17-trimethyl-11-trityloxymethyl-2,3,3a,4,5,6,11,12,15,16,17,17a-dodecahydro-1,13-dioxa-cyclopentacyclohexadecen-14-one

Benzoic acid (2E,4E)-(S)-1-((R)-2-{(2S,3R,5S)-2-[(S)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-5-methoxy-tetrahydro-furan-3-yl}-1-methyl-ethyl)-5-((4R,5R)-4-ethyl-2,2-dimethyl-[1,3]dioxan-5-yl)-4-methyl-penta-2,4-dienyl ester