(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

Base Information

• Chemical Name: (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
• CAS No.: 128828-95-5
• Molecular Formula: C₃₆H₄₇NO₇
• Molecular Weight: 605.772
• Mol file: 128828-95-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 28 articles about (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 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:

2-bromo-3-methylanisole (38197-43-2) → (1R,3R)-3-(4-Benzyloxy-butyl)-1-((1S,2R)-3-benzyloxy-1,2-dihydroxy-propyl)-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (128828-95-5,137038-05-2)

Guidance literature:

Multi-step reaction with 13 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) BuLi / 1) -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

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 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-methylanisole (38197-43-2) → (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)

Guidance literature:

Multi-step reaction with 13 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

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 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,3R)-3-(4-Benzyloxy-butyl)-1-((1S,2R)-3-benzyloxy-1,2-dihydroxy-propyl)-8-methoxy-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (128828-95-5,137038-05-2)

Guidance literature:

Multi-step reaction with 10 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) BuLi / 1) -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

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 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:

di-tert-butyl dicarbonate

3-(4-benzyloxybutyl)-1-<(4S,5R)-5-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-yl>-3-methoxyphenyl-2-hexanone

2-bromo-3-methylanisole

(2-bromo-3-methoxyphenyl)acetic acid

Downstream raw materials:

(1R,3R)-tert-butyl 3-(4-benzyloxybutyl)-8-methoxy-1-methoxymethoxymethyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

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

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

(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