6β-Hydroxy-3,4-dihydromilbemycin E

Base Information

• Chemical Name: 6β-Hydroxy-3,4-dihydromilbemycin E
• CAS No.: 135415-62-2
• Molecular Formula: C₃₄H₅₄O₈
• Molecular Weight: 590.798
• Mol file: 135415-62-2.mol

Synonyms:

Chemical Property of 6β-Hydroxy-3,4-dihydromilbemycin E

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6β-Hydroxy-3,4-dihydromilbemycin E

There total 23 articles about 6β-Hydroxy-3,4-dihydromilbemycin E 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: 74.0%

(4S)-3,4-dihydro-28-oxomilbemycin G (135352-28-2) → 6β-Hydroxy-3,4-dihydromilbemycin E (135415-62-2,145369-50-2)

Guidance literature:

With diisobutylaluminium hydride; In toluene;

DOI:10.1016/S0040-4039(00)79699-7

Reference yield:

ethyl 3-oxo-3-(2'-trimethylsilyl-3'-furyl)propanoate (114047-82-4) → 6β-Hydroxy-3,4-dihydromilbemycin E (135415-62-2,145369-50-2)

Guidance literature:

Multi-step reaction with 18 steps

1: 50 percent / aq. NaOH / ethanol / 20 °C

2: 84 percent / Me₄NBH(OAc)3 / acetic acid; acetonitrile

3: 85 percent / DCC, DMAP

4: 91 percent / H₂ / Pd-C / ethanol

5: 95 percent / (COCl)2, DMSO, Et₃N

6: 95 percent / Me₄NBH(OAc)3

7: 91 percent / Pr₂NEt

8: 87 percent / K₂CO₃ / ethanol

9: 62 percent / Ag₂O

10: 99 percent / NaOH / ethanol

11: 80 percent / DCC, DMAP

12: 88 percent / O₂, TPP / CH₂Cl₂; methanol / Irradiation

14: 92 percent / I₂ / benzene / Irradiation

15: 98 percent / silica / CHCl₃

16: 78 percent / Bu₄NF / tetrahydrofuran

17: DCC, DMAP

18: 74 percent / DIBAL / toluene

With dmap; sodium hydroxide; oxalyl dichloride; dipropylethylamine; tetrabutyl ammonium fluoride; hydrogen; iodine; oxygen; thiamine diphosphate; silica gel; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; silver(l) oxide; tetramethylammonium triacetoxyborohydride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; acetic acid; toluene; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)79699-7

Reference yield:

ethyl (1RS,2SR,3SR,4RS,5SR)-3-benzyloxy-2,4-dihydroxy-5-methyl-2-(2-trimethylsilyl-3-furyl)cyclohexane-1-carboxylate (135352-18-0) → 6β-Hydroxy-3,4-dihydromilbemycin E (135415-62-2,145369-50-2)

Guidance literature:

Multi-step reaction with 16 steps

1: 85 percent / DCC, DMAP

2: 91 percent / H₂ / Pd-C / ethanol

3: 95 percent / (COCl)2, DMSO, Et₃N

4: 95 percent / Me₄NBH(OAc)3

5: 91 percent / Pr₂NEt

6: 87 percent / K₂CO₃ / ethanol

7: 62 percent / Ag₂O

8: 99 percent / NaOH / ethanol

9: 80 percent / DCC, DMAP

10: 88 percent / O₂, TPP / CH₂Cl₂; methanol / Irradiation

12: 92 percent / I₂ / benzene / Irradiation

13: 98 percent / silica / CHCl₃

14: 78 percent / Bu₄NF / tetrahydrofuran

15: DCC, DMAP

16: 74 percent / DIBAL / toluene

With dmap; sodium hydroxide; oxalyl dichloride; dipropylethylamine; tetrabutyl ammonium fluoride; hydrogen; iodine; oxygen; thiamine diphosphate; silica gel; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; silver(l) oxide; tetramethylammonium triacetoxyborohydride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; toluene; benzene;

DOI:10.1016/S0040-4039(00)79699-7

upstream raw materials:

(4S)-3,4-dihydro-28-oxomilbemycin G

(9Z)-9-[(4R,2E,6E)-8-{(2R,3S,6R,8R,10S)-10-hydroxy-3-methyl-2-(1-methylethyl)-1,7-dioxaspiro[5.5]undecan-8-yl}-4,6-dimethylocta-2,6-dienylidene]-1-hydroxy-5-methoxy-4-methyl-8-oxo-7-oxabicyclo[4.3.0]nonane-2-carboxylic acid

3-{8-[4-(tert-butyl-dimethyl-silanyloxy)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-2-yl]-4,6-dimethyl-octa-2,6-dienylidene}-3a-hydroxy-7-methoxy-6-methyl-2-oxo-octahydro-benzofuran-4-carboxylic acid 2-trimethylsilanyl-ethyl ester

methyl (6R,2Z,4E,8E)-10-{(2R,3S,6R,8R,10S)-10-tert-butyldimethylsilyloxy-3-methyl-2-(1-methylethyl)-1,7-dioxaspiro[5.5]undecan-8-yl}-2-[1-(2-trimethylsilylethoxycarbonyl)-2,3-dihydroxy-4-methoxy-5-methyl-cyclohexan-2-yl]-6,8-dimethyldeca-2,4,8-trienoate