(S)-1-[2-{(2R,3R,5S,6R)-6-[(E)-(1S,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-1-methoxy-3,5-dimethyl-deca-5,9-dienyl]-2-hydroxy-5-methoxy-3-methyl-tetrahydro-pyran-2-yl}-2-(4-methoxy-benzyloxy)-acetyl]-piperidine-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (S)-1-[2-{(2R,3R,5S,6R)-6-[(E)-(1S,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-1-methoxy-3,5-dimethyl-deca-5,9-dienyl]-2-hydroxy-5-methoxy-3-methyl-tetrahydro-pyran-2-yl}-2-(4-methoxy-benzyloxy)-acetyl]-piperidine-2-carboxylic acid methyl ester
• CAS No.: 135840-32-3
• Molecular Formula: C₄₄H₇₃NO₁₀Si
• Molecular Weight: 804.15

Synonyms:

Chemical Property of (S)-1-[2-{(2R,3R,5S,6R)-6-[(E)-(1S,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-1-methoxy-3,5-dimethyl-deca-5,9-dienyl]-2-hydroxy-5-methoxy-3-methyl-tetrahydro-pyran-2-yl}-2-(4-methoxy-benzyloxy)-acetyl]-piperidine-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (S)-1-[2-{(2R,3R,5S,6R)-6-[(E)-(1S,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-1-methoxy-3,5-dimethyl-deca-5,9-dienyl]-2-hydroxy-5-methoxy-3-methyl-tetrahydro-pyran-2-yl}-2-(4-methoxy-benzyloxy)-acetyl]-piperidine-2-carboxylic acid methyl ester

There total 33 articles about (S)-1-[2-{(2R,3R,5S,6R)-6-[(E)-(1S,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-1-methoxy-3,5-dimethyl-deca-5,9-dienyl]-2-hydroxy-5-methoxy-3-methyl-tetrahydro-pyran-2-yl}-2-(4-methoxy-benzyloxy)-acetyl]-piperidine-2-carboxylic acid methyl ester 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:

p-methoxybenzyloxy acetic acid (88920-24-5) → (S)-1-[2-{(2R,3R,5S,6R)-6-[(E)-(1S,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-1-methoxy-3,5-dimethyl-deca-5,9-dienyl]-2-hydroxy-5-methoxy-3-methyl-tetrahydro-pyran-2-yl}-2-(4-methoxy-benzyloxy)-acetyl]-piperidine-2-carboxylic acid methyl ester (135840-32-3,135912-33-3)

Guidance literature:

Multi-step reaction with 4 steps

1: DCC / CH₂Cl₂

2: KOH / methanol

3: 1) LDA / 1) THF, -78 deg C 2) -78 to -10 deg C

4: methanol

With potassium hydroxide; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In methanol; dichloromethane;

DOI:10.1016/0040-4039(91)80646-N

Reference yield:

(2S,3S)-4-methyl-2-(2-propenyl)-4-pentene-1,3-diol (186406-55-3) → (S)-1-[2-{(2R,3R,5S,6R)-6-[(E)-(1S,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-1-methoxy-3,5-dimethyl-deca-5,9-dienyl]-2-hydroxy-5-methoxy-3-methyl-tetrahydro-pyran-2-yl}-2-(4-methoxy-benzyloxy)-acetyl]-piperidine-2-carboxylic acid methyl ester (135840-32-3,135912-33-3)

Guidance literature:

Multi-step reaction with 16 steps

1: Et₃N, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

2: DCC, DMAP / CH₂Cl₂ / Ambient temperature

4: 86 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

5: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

6: NaI / acetone / Heating

7: dimethylformamide / 15 h / 80 °C

8: 1) n-BuLi / 1) THF, -78 deg C, 10 min 2) -78 deg C, 2.5 h

9: 1) (COCl)2, DMSO 2) Et₃N / 1) CH₂Cl₂

10: 77 percent / n-Bu₃SnH, AIBN / toluene / Heating

11: 86 percent / DIBAL / toluene / 0.33 h / -78 °C

12: 94 percent / KH / tetrahydrofuran / Ambient temperature

13: 95 percent / Li, NH₃ / tetrahydrofuran / -78 °C

14: 85 percent / pyridinium chlorochromate, MS₄A / CH₂Cl₂ / 2 h / Ambient temperature

15: 1) LDA / 1) THF, -78 deg C 2) -78 to -10 deg C

16: methanol

With dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); ammonia; tri-n-butyl-tin hydride; lithium; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; pyridinium chlorochromate; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/0040-4039(91)80646-N

Reference yield:

(3S,4S)-4-(tert-butyldimethylsilyl)oxymethyl-2-methyl-1,6-heptadien-3-ol (186406-56-4) → (S)-1-[2-{(2R,3R,5S,6R)-6-[(E)-(1S,3S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-1-methoxy-3,5-dimethyl-deca-5,9-dienyl]-2-hydroxy-5-methoxy-3-methyl-tetrahydro-pyran-2-yl}-2-(4-methoxy-benzyloxy)-acetyl]-piperidine-2-carboxylic acid methyl ester (135840-32-3,135912-33-3)

Guidance literature:

Multi-step reaction with 15 steps

1: DCC, DMAP / CH₂Cl₂ / Ambient temperature

3: 86 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

4: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

5: NaI / acetone / Heating

6: dimethylformamide / 15 h / 80 °C

7: 1) n-BuLi / 1) THF, -78 deg C, 10 min 2) -78 deg C, 2.5 h

8: 1) (COCl)2, DMSO 2) Et₃N / 1) CH₂Cl₂

9: 77 percent / n-Bu₃SnH, AIBN / toluene / Heating

10: 86 percent / DIBAL / toluene / 0.33 h / -78 °C

11: 94 percent / KH / tetrahydrofuran / Ambient temperature

12: 95 percent / Li, NH₃ / tetrahydrofuran / -78 °C

13: 85 percent / pyridinium chlorochromate, MS₄A / CH₂Cl₂ / 2 h / Ambient temperature

14: 1) LDA / 1) THF, -78 deg C 2) -78 to -10 deg C

15: methanol

With dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); ammonia; tri-n-butyl-tin hydride; lithium; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; pyridinium chlorochromate; sodium iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/0040-4039(91)80646-N

upstream raw materials:

diazomethane

p-methoxybenzyloxy acetic acid

(2S,3S)-4-methyl-2-(2-propenyl)-4-pentene-1,3-diol

(3S,4S)-4-(tert-butyldimethylsilyl)oxymethyl-2-methyl-1,6-heptadien-3-ol

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