C₇₁H₁₂₅NO₁₂Si₃

Base Information

• Chemical Name: C₇₁H₁₂₅NO₁₂Si₃
• CAS No.: 164592-92-1
• Molecular Formula: C₇₁H₁₂₅NO₁₂Si₃
• Molecular Weight: 1269.03
• Mol file: 164592-92-1.mol

Synonyms:C₇₁H₁₂₅NO₁₂Si₃

Chemical Property of C₇₁H₁₂₅NO₁₂Si₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₇₁H₁₂₅NO₁₂Si₃

There total 43 articles about C₇₁H₁₂₅NO₁₂Si₃ 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:

1-trimethylsilyl-1,3-pentadiyne (18292-02-9) → C71H125NO12Si3 (164592-92-1)

Guidance literature:

Multi-step reaction with 14 steps

1: 1.) CuCN, Bu₃SnH, 2.) n-BuLi / 1.) THF, -20 deg C to room temperature, 4 h, 2.) THF, -78 deg C, 45 min, 3.) THF, -78 deg C, 1 h

2: 89 percent / NaH, 15-crown-5

3: 95 percent / HOAc / tetrahydrofuran; H₂O

4: 99 percent / imidazole / dimethylformamide

5: 72 percent / DIBAL / tetrahydrofuran / -78 - 0 °C

6: 88 percent

7: 1.) LiHMDS / 1.) THF, -78 deg C to 0 deg C, 2.) THF, -78 deg C to 0 deg C

8: 78 percent

9: 77 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / Ambient temperature

10: 80 percent / aq. HF / acetonitrile / Ambient temperature

11: 85 percent / Et₃N

12: 1.) Bu₃SnH, AIBN, 2.) I₂ / 1.) benzene, 90 deg C, 1 h, 2.) CH₂Cl₂, 0 deg C

13: 56 percent / LiI / pyridine / 16 h / 130 °C

14: 1.) EDS, DMAP, DMAP*HCl, 2.) DIPEA, <(2-furyl)3P>2PdCl₂ / 1.) CH₂Cl₂, room temperature, 5 h, 2.) THF, DMF, room temperature, 5 h

With pyridine; 1H-imidazole; dmap; n-butyllithium; 15-crown-5; 2,2'-azobis(isobutyronitrile); dichlorobis(tri(2-furyl)phosphine)palladium(II); hydrogen fluoride; iodine; tri-n-butyl-tin hydride; 4-(dimethylamino)pyridine hydrochloride; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; lithium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja963067o

Reference yield:

triethylsilyl trifluoromethyl sulfonate (79271-56-0) → C71H125NO12Si3 (164592-92-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 99 percent / 2,6-lutidine, Et₃N / CH₂Cl₂ / 5 h / -78 °C

2: 1.) Bu₃SnH, AIBN, 2.) I₂ / 1.) benzene, 90 deg C, 1 h, 2.) CH₂Cl₂, 0 deg C

3: 56 percent / LiI / pyridine / 16 h / 130 °C

4: 1.) EDS, DMAP, DMAP*HCl, 2.) DIPEA, <(2-furyl)3P>2PdCl₂ / 1.) CH₂Cl₂, room temperature, 5 h, 2.) THF, DMF, room temperature, 5 h

With 2,6-dimethylpyridine; dmap; 2,2'-azobis(isobutyronitrile); dichlorobis(tri(2-furyl)phosphine)palladium(II); iodine; tri-n-butyl-tin hydride; 4-(dimethylamino)pyridine hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium iodide; In pyridine; dichloromethane;

DOI:10.1021/ja963067o

Reference yield:

(2R,3R,7S,10R)-7-Allyl-2,3,10-trimethyl-1,4,6-trioxa-spiro[4.5]decane (101977-00-8) → C71H125NO12Si3 (164592-92-1)

Guidance literature:

Multi-step reaction with 15 steps

1: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2.) room temperature, 17.5 h

2: 1.) CuCN, Bu₃SnH, 2.) n-BuLi / 1.) THF, -20 deg C to room temperature, 4 h, 2.) THF, -78 deg C, 45 min, 3.) THF, -78 deg C, 1 h

3: 89 percent / NaH, 15-crown-5

4: 95 percent / HOAc / tetrahydrofuran; H₂O

5: 99 percent / imidazole / dimethylformamide

6: 72 percent / DIBAL / tetrahydrofuran / -78 - 0 °C

7: 88 percent

8: 1.) LiHMDS / 1.) THF, -78 deg C to 0 deg C, 2.) THF, -78 deg C to 0 deg C

9: 78 percent

10: 77 percent / Dess-Martin periodinane, pyridine / CH₂Cl₂ / Ambient temperature

11: 80 percent / aq. HF / acetonitrile / Ambient temperature

12: 85 percent / Et₃N

13: 1.) Bu₃SnH, AIBN, 2.) I₂ / 1.) benzene, 90 deg C, 1 h, 2.) CH₂Cl₂, 0 deg C

14: 56 percent / LiI / pyridine / 16 h / 130 °C

15: 1.) EDS, DMAP, DMAP*HCl, 2.) DIPEA, <(2-furyl)3P>2PdCl₂ / 1.) CH₂Cl₂, room temperature, 5 h, 2.) THF, DMF, room temperature, 5 h

With pyridine; 1H-imidazole; dmap; n-butyllithium; 15-crown-5; 2,2'-azobis(isobutyronitrile); dichlorobis(tri(2-furyl)phosphine)palladium(II); hydrogen fluoride; iodine; tri-n-butyl-tin hydride; 4-(dimethylamino)pyridine hydrochloride; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; ozone; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja963067o

upstream raw materials:

(S)-1-{2-[(2S,3R,6S)-6-((3E,5E)-(S)-6-Iodo-2-methoxy-3-methyl-hexa-3,5-dienyl)-3-methyl-2-triethylsilanyloxy-tetrahydro-pyran-2-yl]-2-oxo-acetyl}-piperidine-2-carboxylic acid

(E)-(2R,3S,6R,9S,12R,14S)-9-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,6,8,12,14-pentamethyl-hexadec-7-en-15-yne-5,11-dione

1-trimethylsilyl-1,3-pentadiyne

triethylsilyl trifluoromethyl sulfonate

Refernces

• 1、 Smith III, Amos B.,Condon, Stephen M.,McCauley, John A.,Leazer Jr., Johnnie L.,Leahy, James W.,Maleczka Jr., Robert E.. "Total synthesis of rapamycin and demethoxyrapamycin". . p. 5407 - 5408. Retrieved 2007/10/02.