C₇₂H₁₂₇NO₁₃Si₃

Base Information

• Chemical Name: C₇₂H₁₂₇NO₁₃Si₃
• CAS No.: 186417-29-8
• Molecular Formula: C₇₂H₁₂₇NO₁₃Si₃
• Molecular Weight: 1299.06
• Mol file: 186417-29-8.mol

Synonyms:C₇₂H₁₂₇NO₁₃Si₃

Chemical Property of C₇₂H₁₂₇NO₁₃Si₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₇₂H₁₂₇NO₁₃Si₃

There total 34 articles about C₇₂H₁₂₇NO₁₃Si₃ 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: 84.0%

t-butyldimethylsiyl triflate (69739-34-0) + C66H113NO13Si2 (186417-28-7) → C72H127NO13Si3 (186417-29-8)

Guidance literature:

With 2,6-dimethylpyridine; trifluoroacetic acid; In dichloromethane; at 0 ℃;

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) → C72H127NO13Si3 (186417-29-8)

Guidance literature:

Multi-step reaction with 17 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.) i-Pr₂NEt, <(2-furyl)3P>2PdCl₂ / 1.) CH₂Cl₂, room temperature, 5 h, 2.) THF, DMF, room temperature, 7 h

16: 90 percent / TBAF, AcOH / tetrahydrofuran / 3 h / 0 °C

17: 84 percent / 2,6-lutidine, TFA / CH₂Cl₂ / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; n-butyllithium; 15-crown-5; 2,2'-azobis(isobutyronitrile); dichlorobis(tri(2-furyl)phosphine)palladium(II); hydrogen fluoride; tetrabutyl ammonium 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; trifluoroacetic acid; lithium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja963067o

Reference yield:

1-trimethylsilyl-1,3-pentadiyne (18292-02-9) → C72H127NO13Si3 (186417-29-8)

Guidance literature:

Multi-step reaction with 16 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.) i-Pr₂NEt, <(2-furyl)3P>2PdCl₂ / 1.) CH₂Cl₂, room temperature, 5 h, 2.) THF, DMF, room temperature, 7 h

15: 90 percent / TBAF, AcOH / tetrahydrofuran / 3 h / 0 °C

16: 84 percent / 2,6-lutidine, TFA / CH₂Cl₂ / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; n-butyllithium; 15-crown-5; 2,2'-azobis(isobutyronitrile); dichlorobis(tri(2-furyl)phosphine)palladium(II); hydrogen fluoride; tetrabutyl ammonium 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; trifluoroacetic acid; lithium iodide; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja963067o

upstream raw materials:

t-butyldimethylsiyl triflate

C₆₆H₁₁₃NO₁₃Si₂

1-trimethylsilyl-1,3-pentadiyne

(2R,3R,7S,10R)-7-Allyl-2,3,10-trimethyl-1,4,6-trioxa-spiro[4.5]decane

Downstream raw materials:

C₆₆H₁₁₃NO₁₃Si₂

sirolimus

C₇₂H₁₂₇NO₁₃Si₃

C₆₉H₁₂₁NO₁₃Si₃