(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 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

Base Information

Chemical Name:(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 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester
CAS No.:135708-89-3
Molecular Formula:C₅₁H₇₃NO₉Si₂
Molecular Weight:900.313
Hs Code.:

(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 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

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Chemical Property of (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 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

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Technology Process of (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 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

There total 13 articles about (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 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester 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:

: 89046-67-3,91796-47-3,91796-48-4,91798-02-6,91798-03-7,94233-73-5,94233-74-6,106357-32-8
(5R)-6-benzyloxy-5-methyl-4-hydroxyhex-1-ene

: 135708-89-3,135818-60-9
(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 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

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

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:

: 135708-75-7,135708-76-8
[1-((R)-2-Benzyloxy-1-methyl-ethyl)-but-3-enyloxy]-tert-butyl-dimethyl-silane

: 135708-89-3,135818-60-9
(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 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

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

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:

: 135708-77-9,135708-78-0
(R)-5-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentanal

: 135708-89-3,135818-60-9
(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 1,3-dioxo-1,3-dihydro-isoindol-2-yl ester

Guidance literature:: Multi-step reaction with 11 steps

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

2: Bu₄NF / tetrahydrofuran / 2 h / Ambient temperature

3: 93 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

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

5: 90 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂

6: 99 percent / KMnO₄, NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O

7: 75 percent / 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide (EDCI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 16 h / Ambient temperature

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

9: toluene / 2 h / Heating

10: 0.1N aq.LiOH / tetrahydrofuran / 2 h

11: 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide (EDCI), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 8 h

With 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; tetrabutyl ammonium fluoride; dihydrogen peroxide; 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