(3R,4R,5E)-6-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienylcarbamoyl)-2,4-dimethylhex-5-en-3-yl 2,2,2-trichloroethyl (2R)-pyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (3R,4R,5E)-6-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienylcarbamoyl)-2,4-dimethylhex-5-en-3-yl 2,2,2-trichloroethyl (2R)-pyrrolidine-1,2-dicarboxylate
• CAS No.: 175551-72-1
• Molecular Formula: C₄₈H₇₁Cl₃N₂O₇Si₂
• Molecular Weight: 950.631
• Mol file: 175551-72-1.mol

Synonyms:(3R,4R,5E)-6-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienylcarbamoyl)-2,4-dimethylhex-5-en-3-yl 2,2,2-trichloroethyl (2R)-pyrrolidine-1,2-dicarboxylate

Chemical Property of (3R,4R,5E)-6-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienylcarbamoyl)-2,4-dimethylhex-5-en-3-yl 2,2,2-trichloroethyl (2R)-pyrrolidine-1,2-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5E)-6-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienylcarbamoyl)-2,4-dimethylhex-5-en-3-yl 2,2,2-trichloroethyl (2R)-pyrrolidine-1,2-dicarboxylate

There total 41 articles about (3R,4R,5E)-6-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienylcarbamoyl)-2,4-dimethylhex-5-en-3-yl 2,2,2-trichloroethyl (2R)-pyrrolidine-1,2-dicarboxylate 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: 89.0%

(E,4R,5R)-5-((R)-1-((2,2,2-trichloroethoxy)carbonyl)pyrrolidine-2-carbonyloxy)-4,6-dimethylhept-2-enoic acid (175551-63-0) + (S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dien-1-amine (175551-71-0) → (3R,4R,5E)-6-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienylcarbamoyl)-2,4-dimethylhex-5-en-3-yl 2,2,2-trichloroethyl (2R)-pyrrolidine-1,2-dicarboxylate (175551-72-1)

Guidance literature:

With tributyl-amine; 2-chloro-1-methyl-pyridinium iodide; In dichloromethane; Ambient temperature;

DOI:10.1021/ja954311z

Reference yield:

3-(tert-butyldimethylsilanyloxy)propionaldehyde (89922-82-7) → (3R,4R,5E)-6-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienylcarbamoyl)-2,4-dimethylhex-5-en-3-yl 2,2,2-trichloroethyl (2R)-pyrrolidine-1,2-dicarboxylate (175551-72-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 65 percent / CH₂Cl₂ / 3 h / Heating

2: K₃Fe(CN)6; K₂CO₃; MeSO₂NH₂ / OsO₄; (DHQ)2PHAL / 2-methyl-propan-2-ol / 5 h / 0 °C

3: pyridine / CH₂Cl₂ / cooling

4: potassium tert-butoxide / tetrahydrofuran / 0.42 h / -40 °C

5: LiOH / tetrahydrofuran; H₂O / 3 h / 45 °C

6: camphorsulfonic acid / CH₂Cl₂; acetone / 0.42 h

7: DIBAL / tetrahydrofuran / 0.17 h / -78 °C

8: triphenylphosphine; imidazole; I₂ / acetonitrile / 0.03 h

9: acetonitrile / 3.5 h / Heating

10: 30 mg / K₂CO₃ / methanol / 3.5 h / 20 °C

11: 89 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

12: 70 percent / AlH₃ / tetrahydrofuran / 1 h / 0 °C

13: 82 percent / N,N'-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

With pyridine; 1H-imidazole; aluminium hydride; dmap; lithium hydroxide; methanesulfonamide; camphor-10-sulfonic acid; potassium tert-butylate; iodine; diisobutylaluminium hydride; potassium carbonate; dicyclohexyl-carbodiimide; triphenylphosphine; potassium hexacyanoferrate(III); osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol; 1: Wittig reaction / 2: Sharpless dihydroxylation / 4: Horner-Emmons olefination;

DOI:10.1021/ol071145e

Reference yield:

3-tert-butyldimethylsilyloxy-1-propanol (73842-99-6) → (3R,4R,5E)-6-((S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienylcarbamoyl)-2,4-dimethylhex-5-en-3-yl 2,2,2-trichloroethyl (2R)-pyrrolidine-1,2-dicarboxylate (175551-72-1)

Guidance literature:

Multi-step reaction with 14 steps

1: 99 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 3 h / -78 °C

2: 65 percent / CH₂Cl₂ / 3 h / Heating

3: K₃Fe(CN)6; K₂CO₃; MeSO₂NH₂ / OsO₄; (DHQ)2PHAL / 2-methyl-propan-2-ol / 5 h / 0 °C

4: pyridine / CH₂Cl₂ / cooling

5: potassium tert-butoxide / tetrahydrofuran / 0.42 h / -40 °C

6: LiOH / tetrahydrofuran; H₂O / 3 h / 45 °C

7: camphorsulfonic acid / CH₂Cl₂; acetone / 0.42 h

8: DIBAL / tetrahydrofuran / 0.17 h / -78 °C

9: triphenylphosphine; imidazole; I₂ / acetonitrile / 0.03 h

10: acetonitrile / 3.5 h / Heating

11: 30 mg / K₂CO₃ / methanol / 3.5 h / 20 °C

12: 89 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

13: 70 percent / AlH₃ / tetrahydrofuran / 1 h / 0 °C

14: 82 percent / N,N'-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

With pyridine; 1H-imidazole; aluminium hydride; dmap; lithium hydroxide; oxalyl dichloride; methanesulfonamide; camphor-10-sulfonic acid; potassium tert-butylate; iodine; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; potassium hexacyanoferrate(III); osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol; 1: Swern oxidation / 2: Wittig reaction / 3: Sharpless dihydroxylation / 5: Horner-Emmons olefination;

DOI:10.1021/ol071145e

upstream raw materials:

(E,4R,5R)-5-((R)-1-((2,2,2-trichloroethoxy)carbonyl)pyrrolidine-2-carbonyloxy)-4,6-dimethylhept-2-enoic acid

(S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dien-1-amine

ethyl (E,4R,5R)-4,5-dihydroxy-4,6-dimethylhept-2-enoate

ethyl (E)-3-((4S,5S)-5-(2-(tert-butyldimethylsilyloxy)ethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-enoate

Downstream raw materials:

(12E,17E,19E)-(7R,10R,11R,21S)-21-(tert-Butyl-diphenyl-silanyloxy)-10-isopropyl-11,19-dimethyl-9,26-dioxa-3,15,28-triaza-tricyclo[23.2.1.0^3,7]octacosa-1⁽²⁷⁾,12,17,19,25⁽²⁸⁾-pentaene-2,8,14,23-tetraone

(R)-Pyrrolidine-1,2-dicarboxylic acid 2-{(E)-(1R,2R)-4-[(2E,4E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-4-methyl-8-oxo-octa-2,4-dienylcarbamoyl]-1-isopropyl-2-methyl-but-3-enyl} ester 1-(2,2,2-trichloro-ethyl) ester

virginiamycin M2

(R)-Pyrrolidine-1,2-dicarboxylic acid 2-{(E)-(1R,2R)-4-[(2E,4E)-(S)-6-(tert-butyl-diphenyl-silanyloxy)-8-hydroxy-4-methyl-octa-2,4-dienylcarbamoyl]-1-isopropyl-2-methyl-but-3-enyl} ester 1-(2,2,2-trichloro-ethyl) ester

Refernces

• 1、 Schlessinger,Li. "Total synthesis of (-)-virginiamycin M2 using second-generation vinylogous urethane chemistry". . p. 3301 - 3302. Retrieved 2007/10/03.