(1R,5S,10bS)-5-(4-Benzyloxy-butyl)-1-((S)-2-benzyloxy-1-hydroxy-ethyl)-10-methoxy-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-3-one

Base Information

• Chemical Name: (1R,5S,10bS)-5-(4-Benzyloxy-butyl)-1-((S)-2-benzyloxy-1-hydroxy-ethyl)-10-methoxy-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-3-one
• CAS No.: 128829-01-6
• Molecular Formula: C₃₂H₃₇NO₆
• Molecular Weight: 531.649
• Mol file: 128829-01-6.mol

Synonyms:(1R,5S,10bS)-5-(4-Benzyloxy-butyl)-1-((S)-2-benzyloxy-1-hydroxy-ethyl)-10-methoxy-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-3-one

Chemical Property of (1R,5S,10bS)-5-(4-Benzyloxy-butyl)-1-((S)-2-benzyloxy-1-hydroxy-ethyl)-10-methoxy-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5S,10bS)-5-(4-Benzyloxy-butyl)-1-((S)-2-benzyloxy-1-hydroxy-ethyl)-10-methoxy-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-3-one

There total 15 articles about (1R,5S,10bS)-5-(4-Benzyloxy-butyl)-1-((S)-2-benzyloxy-1-hydroxy-ethyl)-10-methoxy-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-3-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: 72.0%

(1S,3S)-3-(4-Benzyloxy-butyl)-1-((1R,2S)-3-benzyloxy-1,2-dihydroxy-propyl)-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (128828-95-5) → (1R,5S,10bS)-5-(4-Benzyloxy-butyl)-1-((S)-2-benzyloxy-1-hydroxy-ethyl)-10-methoxy-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-3-one (128829-01-6)

Guidance literature:

With sodium hydride; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(00)70714-3

Reference yield:

2-bromo-3-methylanisole (38197-43-2) → (1R,5S,10bS)-5-(4-Benzyloxy-butyl)-1-((S)-2-benzyloxy-1-hydroxy-ethyl)-10-methoxy-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-3-one (128829-01-6)

Guidance literature:

Multi-step reaction with 14 steps

1: Br₂ / CCl₄ / Ambient temperature; Irradiation

2: dimethylsulfoxide / Ambient temperature

3: KOH / methanol / Heating

4: diethyl ether / Ambient temperature

5: 1)LDA, 2) DABCO / 1) THF, -78 deg C, 2) -78 deg C, 3) -78 deg C

6: 93 percent / Jones reagent

7: 90 percent / NaCl, DMSO / H₂O / 140 °C

8: CSA / methanol / Heating

9: 1) nBuLi / 1) ether, -78 deg C, 2) ether, -78 deg C to 0 deg C

10: CrO₃-2Py, MS₃A / CH₂Cl₂ / Ambient temperature

11: 1N HCl / tetrahydrofuran / Ambient temperature

12: 14N aq. NH₃ / tetrahydrofuran / Ambient temperature

13: 1) NaBH₃CN, 0.1N HCl, 2) 12N HCl, 3) 6N NaOH / 1) MeOH, 0 deg C, 2) MeOH, rt., 3) CHCl₃, reflux

14: 72 percent / NaH / tetrahydrofuran / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; potassium hydroxide; ammonium hydroxide; sodium hydroxide; n-butyllithium; jones reagent; camphor-10-sulfonic acid; bromine; dipyridine chromium trioxide; sodium hydride; sodium cyanoborohydride; dimethyl sulfoxide; sodium chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)70714-3

Reference yield:

(2-bromo-3-methoxyphenyl)acetic acid (54639-89-3) → (1R,5S,10bS)-5-(4-Benzyloxy-butyl)-1-((S)-2-benzyloxy-1-hydroxy-ethyl)-10-methoxy-1,5,6,10b-tetrahydro-oxazolo[4,3-a]isoquinolin-3-one (128829-01-6)

Guidance literature:

Multi-step reaction with 11 steps

1: diethyl ether / Ambient temperature

2: 1)LDA, 2) DABCO / 1) THF, -78 deg C, 2) -78 deg C, 3) -78 deg C

3: 93 percent / Jones reagent

4: 90 percent / NaCl, DMSO / H₂O / 140 °C

5: CSA / methanol / Heating

6: 1) nBuLi / 1) ether, -78 deg C, 2) ether, -78 deg C to 0 deg C

7: CrO₃-2Py, MS₃A / CH₂Cl₂ / Ambient temperature

8: 1N HCl / tetrahydrofuran / Ambient temperature

9: 14N aq. NH₃ / tetrahydrofuran / Ambient temperature

10: 1) NaBH₃CN, 0.1N HCl, 2) 12N HCl, 3) 6N NaOH / 1) MeOH, 0 deg C, 2) MeOH, rt., 3) CHCl₃, reflux

11: 72 percent / NaH / tetrahydrofuran / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; hydrogenchloride; ammonium hydroxide; sodium hydroxide; n-butyllithium; jones reagent; camphor-10-sulfonic acid; dipyridine chromium trioxide; sodium hydride; sodium cyanoborohydride; dimethyl sulfoxide; sodium chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

DOI:10.1016/S0040-4039(00)70714-3

upstream raw materials:

(1S,3S)-3-(4-Benzyloxy-butyl)-1-((1R,2S)-3-benzyloxy-1,2-dihydroxy-propyl)-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester

2-bromo-3-methylanisole

(2-bromo-3-methoxyphenyl)acetic acid

5-benzyloxy-1-pentanal