benzyl ((1R,3S)-8-hydroxy-3-(hydroxymethyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate

Base Information

Chemical Name:benzyl ((1R,3S)-8-hydroxy-3-(hydroxymethyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate
CAS No.:1310875-39-8
Molecular Formula:C₂₁H₂₆N₂O₅
Molecular Weight:386.448
Hs Code.:

Synonyms:benzyl ((1R,3S)-8-hydroxy-3-(hydroxymethyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate

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Chemical Property of benzyl ((1R,3S)-8-hydroxy-3-(hydroxymethyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate

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Technology Process of benzyl ((1R,3S)-8-hydroxy-3-(hydroxymethyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate

There total 1 articles about benzyl ((1R,3S)-8-hydroxy-3-(hydroxymethyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate 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: 86.0%

: 67561-03-9
N-benzyloxycarbonylglycinal

: 686776-27-2
(S)-5-(2-amino-3-hydroxypropyl)-2-methoxy-3-methylphenol

: 1310875-39-8
benzyl ((1R,3S)-8-hydroxy-3-(hydroxymethyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate

Guidance literature:: With acetic acid; In dichloromethane; 2,2,2-trifluoroethanol; at 0 ℃; for 10h; stereospecific reaction; Inert atmosphere; Molecular sieve;
DOI:10.1021/jo200758r

Reference yield: 91.0%

: 1310875-39-8
benzyl ((1R,3S)-8-hydroxy-3-(hydroxymethyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1310875-40-1
benzyl ((1R,3S)-8-(tert-butyldimethylsilyloxy)-3-((tert-butyldimethylsilyloxy)methyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 48h; Inert atmosphere;
DOI:10.1021/jo200758r

Reference yield:

: 1310875-39-8
benzyl ((1R,3S)-8-hydroxy-3-(hydroxymethyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methylcarbamate

: 1310875-44-5
C₃₇H₄₄BrN₃O₁₀

Guidance literature:: Multi-step reaction with 5 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere

2: bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine / dichloromethane / 72 h / 20 °C / Cooling with ice

3: formic acid / tetrahydrofuran; water / 10 h / 20 °C

4: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 20 °C

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; formic acid; tetrabutyl ammonium fluoride; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo200758r