(4R,5S)-5-[(2S,3R)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3-((1S,4R,5R)-4-benzyloxy-5-methoxy-cyclohex-2-enyl)-4-methyl-dihydro-furan-2-one

Base Information

• Chemical Name: (4R,5S)-5-[(2S,3R)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3-((1S,4R,5R)-4-benzyloxy-5-methoxy-cyclohex-2-enyl)-4-methyl-dihydro-furan-2-one
• CAS No.: 135708-88-2
• Molecular Formula: C₃₇H₅₄O₆Si
• Molecular Weight: 622.918

Synonyms:

Chemical Property of (4R,5S)-5-[(2S,3R)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3-((1S,4R,5R)-4-benzyloxy-5-methoxy-cyclohex-2-enyl)-4-methyl-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-5-[(2S,3R)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3-((1S,4R,5R)-4-benzyloxy-5-methoxy-cyclohex-2-enyl)-4-methyl-dihydro-furan-2-one

There total 13 articles about (4R,5S)-5-[(2S,3R)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3-((1S,4R,5R)-4-benzyloxy-5-methoxy-cyclohex-2-enyl)-4-methyl-dihydro-furan-2-one 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: 70.0%

(3R,4S,6S,7R)-8-Benzyloxy-2-((1S,4R,5R)-4-benzyloxy-5-methoxy-cyclohex-2-enyl)-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid (135708-87-1,135818-58-5) → (4R,5S)-5-[(2S,3R)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3-((1S,4R,5R)-4-benzyloxy-5-methoxy-cyclohex-2-enyl)-4-methyl-dihydro-furan-2-one (135708-88-2,135818-59-6,151062-51-0)

Guidance literature:

With dmap; oxalyl dichloride; In dichloromethane;

DOI:10.1016/S0040-4039(00)60597-X

Reference yield:

(5R)-6-benzyloxy-5-methyl-4-hydroxyhex-1-ene (89046-67-3,91796-47-3,91796-48-4,91798-02-6,91798-03-7,94233-73-5,94233-74-6,106357-32-8) → (4R,5S)-5-[(2S,3R)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3-((1S,4R,5R)-4-benzyloxy-5-methoxy-cyclohex-2-enyl)-4-methyl-dihydro-furan-2-one (135708-88-2,135818-59-6,151062-51-0)

Guidance literature:

Multi-step reaction with 13 steps

1: 98 percent / imidazole / dimethylformamide / 48 h / Ambient temperature

2: 1) O₃, pyridine, 2) DMS / 1) MeOH, CH₂Cl₂, -78 deg C, 2) r.t., 15 h

3: 2) 15percent aq.NaOH / 1) toluene, -78 deg C, 2 h, 2) r.t., 16 h

4: Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

5: 93 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

6: 1) 9-BBN, 2) 30percent H₂O₂, 3M NaOH / 1) THF, r.t., 4 h, 2) 0 deg C, 1 h

7: 90 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂

8: 99 percent / KMnO₄, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O

9: 75 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide (EDCI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 16 h / Ambient temperature

10: 1) LDA, HMPA / 1) THF, hexane, -78 deg C, 15 min, 2) THF, r.t., 0.5 h

11: toluene / 2 h / Heating

12: 0.1N aq.LiOH / tetrahydrofuran / 2 h

13: Barton conditions

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; sodium hydroxide; potassium permanganate; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; 2,3-dimercapto-succinic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; ozone; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/jo00020a026

Reference yield:

[1-((R)-2-Benzyloxy-1-methyl-ethyl)-but-3-enyloxy]-tert-butyl-dimethyl-silane (135708-75-7,135708-76-8) → (4R,5S)-5-[(2S,3R)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3-((1S,4R,5R)-4-benzyloxy-5-methoxy-cyclohex-2-enyl)-4-methyl-dihydro-furan-2-one (135708-88-2,135818-59-6,151062-51-0)

Guidance literature:

Multi-step reaction with 12 steps

1: 1) O₃, pyridine, 2) DMS / 1) MeOH, CH₂Cl₂, -78 deg C, 2) r.t., 15 h

2: 2) 15percent aq.NaOH / 1) toluene, -78 deg C, 2 h, 2) r.t., 16 h

3: Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

4: 93 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

5: 1) 9-BBN, 2) 30percent H₂O₂, 3M NaOH / 1) THF, r.t., 4 h, 2) 0 deg C, 1 h

6: 90 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂

7: 99 percent / KMnO₄, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O

8: 75 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide (EDCI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 16 h / Ambient temperature

9: 1) LDA, HMPA / 1) THF, hexane, -78 deg C, 15 min, 2) THF, r.t., 0.5 h

10: toluene / 2 h / Heating

11: 0.1N aq.LiOH / tetrahydrofuran / 2 h

12: Barton conditions

With pyridine; 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; lithium hydroxide; sodium hydroxide; potassium permanganate; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; 2,3-dimercapto-succinic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; ozone; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1021/jo00020a026

upstream raw materials:

(3R,4S,6S,7R)-8-Benzyloxy-2-((1S,4R,5R)-4-benzyloxy-5-methoxy-cyclohex-2-enyl)-4,6-bis-(tert-butyl-dimethyl-silanyloxy)-3,7-dimethyl-octanoic acid

(5R)-6-benzyloxy-5-methyl-4-hydroxyhex-1-ene

[1-((R)-2-Benzyloxy-1-methyl-ethyl)-but-3-enyloxy]-tert-butyl-dimethyl-silane

(R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanal

Downstream raw materials:

(4R,5S)-5-[(2S,3R)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-butyl]-3-((1R,3R,4R)-4-benzyloxy-3-methoxy-cyclohexyl)-4-methyl-tetrahydro-furan-2-ol

Formic acid (1S,3S,4R)-5-benzyloxy-1-[(S)-2-((1R,3R,4R)-4-benzyloxy-3-methoxy-cyclohexyl)-2-iodo-1-methyl-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentyl ester

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