4-(tert-butyl-diphenyl-silanyloxy)-pent-2-enoic acid (6-{5-[3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-6-methyl-4-methylene-tetrahydro-pyran-2-yl]-3-methyl-penta-2,4-dienyl}-2,5-dimethyl-tetrahydro-pyran-3-yl)-amide

Base Information

• Chemical Name: 4-(tert-butyl-diphenyl-silanyloxy)-pent-2-enoic acid (6-{5-[3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-6-methyl-4-methylene-tetrahydro-pyran-2-yl]-3-methyl-penta-2,4-dienyl}-2,5-dimethyl-tetrahydro-pyran-3-yl)-amide
• CAS No.: 391611-34-0
• Molecular Formula: C₄₈H₇₃NO₆Si₂
• Molecular Weight: 816.282

Synonyms:

Chemical Property of 4-(tert-butyl-diphenyl-silanyloxy)-pent-2-enoic acid (6-{5-[3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-6-methyl-4-methylene-tetrahydro-pyran-2-yl]-3-methyl-penta-2,4-dienyl}-2,5-dimethyl-tetrahydro-pyran-3-yl)-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(tert-butyl-diphenyl-silanyloxy)-pent-2-enoic acid (6-{5-[3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-6-methyl-4-methylene-tetrahydro-pyran-2-yl]-3-methyl-penta-2,4-dienyl}-2,5-dimethyl-tetrahydro-pyran-3-yl)-amide

There total 32 articles about 4-(tert-butyl-diphenyl-silanyloxy)-pent-2-enoic acid (6-{5-[3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-6-methyl-4-methylene-tetrahydro-pyran-2-yl]-3-methyl-penta-2,4-dienyl}-2,5-dimethyl-tetrahydro-pyran-3-yl)-amide 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:

(4R,5R)-4-t-butoxycarbonylamino-2-methylhexan-5-olide (263881-01-2) → 4-(tert-butyl-diphenyl-silanyloxy)-pent-2-enoic acid (6-{5-[3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-6-methyl-4-methylene-tetrahydro-pyran-2-yl]-3-methyl-penta-2,4-dienyl}-2,5-dimethyl-tetrahydro-pyran-3-yl)-amide (391611-34-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 65 percent / Lawesson's reagent / toluene / 7 h / 80 °C

2.1: 81 percent / toluene / 24 h / 80 °C

3.1: 100 percent / DBU / benzene / 6 h / Heating

4.1: 68 percent / H₂ / PtO₂ / acetic acid / 24 h / 3040 Torr

5.1: 94 percent / DIBAL / toluene / -70 °C

6.1: 97 percent / benzene / 6 h / Heating

7.1: 82 percent / DIBAL / toluene / -78 - 20 °C

8.1: 90 percent / CBr₄; PPh₃ / CH₂Cl₂

9.1: 87 percent / dimethylformamide / 17 h

10.1: 100 percent / 4N HCl / ethyl acetate

11.1: 86 percent / HBTU; N-ethylmorpholine / acetonitrile / 12 h

12.1: n-BuLi / tetrahydrofuran / -78 °C

12.2: BzCl / tetrahydrofuran / -78 °C

12.3: Na(Hg) / tetrahydrofuran; methanol / -20 °C

With Lawessons reagent; N-ethylmorpholine;; hydrogenchloride; n-butyllithium; carbon tetrabromide; hydrogen; diisobutylaluminium hydride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; platinum(IV) oxide; In tetrahydrofuran; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 2.1: Wittig reaction / 6.1: Wittig reaction / 12.1: Julia olefination;

DOI:10.1016/S0040-4039(01)01763-4

Reference yield:

(3R,5R,6R)-5-t-butoxycarbonylamino-3,6-dimethyltetrahydropyran-2-thione (391611-26-0) → 4-(tert-butyl-diphenyl-silanyloxy)-pent-2-enoic acid (6-{5-[3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-6-methyl-4-methylene-tetrahydro-pyran-2-yl]-3-methyl-penta-2,4-dienyl}-2,5-dimethyl-tetrahydro-pyran-3-yl)-amide (391611-34-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 81 percent / toluene / 24 h / 80 °C

2.1: 100 percent / DBU / benzene / 6 h / Heating

3.1: 68 percent / H₂ / PtO₂ / acetic acid / 24 h / 3040 Torr

4.1: 94 percent / DIBAL / toluene / -70 °C

5.1: 97 percent / benzene / 6 h / Heating

6.1: 82 percent / DIBAL / toluene / -78 - 20 °C

7.1: 90 percent / CBr₄; PPh₃ / CH₂Cl₂

8.1: 87 percent / dimethylformamide / 17 h

9.1: 100 percent / 4N HCl / ethyl acetate

10.1: 86 percent / HBTU; N-ethylmorpholine / acetonitrile / 12 h

11.1: n-BuLi / tetrahydrofuran / -78 °C

11.2: BzCl / tetrahydrofuran / -78 °C

11.3: Na(Hg) / tetrahydrofuran; methanol / -20 °C

With N-ethylmorpholine;; hydrogenchloride; n-butyllithium; carbon tetrabromide; hydrogen; diisobutylaluminium hydride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; platinum(IV) oxide; In tetrahydrofuran; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 1.1: Wittig reaction / 5.1: Wittig reaction / 11.1: Julia olefination;

DOI:10.1016/S0040-4039(01)01763-4

Reference yield:

(4R,5R)-4-((E)-2-Ethoxycarbonyl-propenyl)-2,2,5-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (391611-37-3) → 4-(tert-butyl-diphenyl-silanyloxy)-pent-2-enoic acid (6-{5-[3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-6-methyl-4-methylene-tetrahydro-pyran-2-yl]-3-methyl-penta-2,4-dienyl}-2,5-dimethyl-tetrahydro-pyran-3-yl)-amide (391611-34-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 100 percent / H₂ / Pd(OH)2/C / propan-2-ol / 6 h

2.1: CSA / methanol / 12 h

2.2: CSA / benzene

3.1: 65 percent / Lawesson's reagent / toluene / 7 h / 80 °C

4.1: 81 percent / toluene / 24 h / 80 °C

5.1: 100 percent / DBU / benzene / 6 h / Heating

6.1: 68 percent / H₂ / PtO₂ / acetic acid / 24 h / 3040 Torr

7.1: 94 percent / DIBAL / toluene / -70 °C

8.1: 97 percent / benzene / 6 h / Heating

9.1: 82 percent / DIBAL / toluene / -78 - 20 °C

10.1: 90 percent / CBr₄; PPh₃ / CH₂Cl₂

11.1: 87 percent / dimethylformamide / 17 h

12.1: 100 percent / 4N HCl / ethyl acetate

13.1: 86 percent / HBTU; N-ethylmorpholine / acetonitrile / 12 h

14.1: n-BuLi / tetrahydrofuran / -78 °C

14.2: BzCl / tetrahydrofuran / -78 °C

14.3: Na(Hg) / tetrahydrofuran; methanol / -20 °C

With Lawessons reagent; N-ethylmorpholine;; hydrogenchloride; n-butyllithium; carbon tetrabromide; camphor-10-sulfonic acid; hydrogen; diisobutylaluminium hydride; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; platinum(IV) oxide; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; isopropyl alcohol; toluene; acetonitrile; benzene; 4.1: Wittig reaction / 8.1: Wittig reaction / 14.1: Julia olefination;

DOI:10.1016/S0040-4039(01)01763-4

upstream raw materials:

(2S,3S,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-methoxy-6-methyl-4-methylene-tetrahydro-pyran-2-carbaldehyde

(Z)-(S)-4-(tert-Butyl-diphenyl-silanyloxy)-pent-2-enoic acid {(2R,3R,5S,6S)-2,5-dimethyl-6-[(E)-3-methyl-4-(toluene-4-sulfonyl)-but-2-enyl]-tetrahydro-pyran-3-yl}-amide

2-deoxy-D-arabino-hexopyranose

t-butyldimethylsiyl triflate

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