(1R,3S)-2-chloroethyl 8-(benzyloxy)-1-[(R)-1-({(R)-1-[6-(benzyloxy)-7-{[(trifluoromethyl)sulfonyl]oxy}benzo[d][1,3]dioxol-4-yl]-2-hydroxyethyl}amino)-2-{(tert-butyldimethylsilyl)oxy}ethyl]-3-(dimethoxymethyl)-7-methoxy-6-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Base Information

• Chemical Name: (1R,3S)-2-chloroethyl 8-(benzyloxy)-1-[(R)-1-({(R)-1-[6-(benzyloxy)-7-{[(trifluoromethyl)sulfonyl]oxy}benzo[d][1,3]dioxol-4-yl]-2-hydroxyethyl}amino)-2-{(tert-butyldimethylsilyl)oxy}ethyl]-3-(dimethoxymethyl)-7-methoxy-6-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
• CAS No.: 1414948-78-9
• Molecular Formula: C₄₉H₆₂ClF₃N₂O₁₄SSi
• Molecular Weight: 1055.64

Synonyms:(1R,3S)-2-chloroethyl 8-(benzyloxy)-1-[(R)-1-({(R)-1-[6-(benzyloxy)-7-{[(trifluoromethyl)sulfonyl]oxy}benzo[d][1,3]dioxol-4-yl]-2-hydroxyethyl}amino)-2-{(tert-butyldimethylsilyl)oxy}ethyl]-3-(dimethoxymethyl)-7-methoxy-6-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Chemical Property of (1R,3S)-2-chloroethyl 8-(benzyloxy)-1-[(R)-1-({(R)-1-[6-(benzyloxy)-7-{[(trifluoromethyl)sulfonyl]oxy}benzo[d][1,3]dioxol-4-yl]-2-hydroxyethyl}amino)-2-{(tert-butyldimethylsilyl)oxy}ethyl]-3-(dimethoxymethyl)-7-methoxy-6-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

Chemical Property:

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Technology Process of (1R,3S)-2-chloroethyl 8-(benzyloxy)-1-[(R)-1-({(R)-1-[6-(benzyloxy)-7-{[(trifluoromethyl)sulfonyl]oxy}benzo[d][1,3]dioxol-4-yl]-2-hydroxyethyl}amino)-2-{(tert-butyldimethylsilyl)oxy}ethyl]-3-(dimethoxymethyl)-7-methoxy-6-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate

There total 20 articles about (1R,3S)-2-chloroethyl 8-(benzyloxy)-1-[(R)-1-({(R)-1-[6-(benzyloxy)-7-{[(trifluoromethyl)sulfonyl]oxy}benzo[d][1,3]dioxol-4-yl]-2-hydroxyethyl}amino)-2-{(tert-butyldimethylsilyl)oxy}ethyl]-3-(dimethoxymethyl)-7-methoxy-6-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 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: 91.0%

(1R,3S)-2-chloroethyl 8-(benzyloxy)-1-{(4R,6R)-4-[6-(benzyloxy)-7-{[(trifluoromethyl)sulfonyl]oxy}benzo[d][1,3]dioxol-4-yl]-9,9,10,10-tetramethyl-3-oxo-2,8-dioxa-5-aza-9-silaundecan-6-yl}-3-(dimethoxymethyl)-7-methoxy-6-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (1414948-76-7) → (1R,3S)-2-chloroethyl 8-(benzyloxy)-1-[(R)-1-({(R)-1-[6-(benzyloxy)-7-{[(trifluoromethyl)sulfonyl]oxy}benzo[d][1,3]dioxol-4-yl]-2-hydroxyethyl}amino)-2-{(tert-butyldimethylsilyl)oxy}ethyl]-3-(dimethoxymethyl)-7-methoxy-6-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (1414948-78-9)

Guidance literature:

With sodium tetrahydroborate; lithium chloride; In tetrahydrofuran; ethanol; at 0 - 20 ℃; for 48h;

DOI:10.1055/s-0032-1316579

Reference yield:

(S)-5-(2-amino-3,3-dimethoxypropyl)-2-methoxy-3-methylphenol (1414948-46-1) → (1R,3S)-2-chloroethyl 8-(benzyloxy)-1-[(R)-1-({(R)-1-[6-(benzyloxy)-7-{[(trifluoromethyl)sulfonyl]oxy}benzo[d][1,3]dioxol-4-yl]-2-hydroxyethyl}amino)-2-{(tert-butyldimethylsilyl)oxy}ethyl]-3-(dimethoxymethyl)-7-methoxy-6-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (1414948-78-9)

Guidance literature:

Multi-step reaction with 11 steps

1: formic acid; sodium sulfate / dichloromethane / 24 h / 0 - 20 °C

2: potassium carbonate / acetone / 41.5 h / 0 - 20 °C

3: pyridine / dichloromethane / 1 h / 0 - 20 °C

4: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetonitrile / 2 h / 0 - 20 °C

5: N-ethyl-N,N-diisopropylamine / acetonitrile / 23.5 h / 0 - 20 °C

6: N-Bromosuccinimide / dichloromethane / 0.5 h / 0 °C

7: trifluoroacetic acid / dichloromethane / 0.42 h / 0 °C

8: pyridine / dichloromethane / 0.5 h / 0 °C

9: triethylamine / 1 h / 20 °C

10: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 0 - 20 °C

11: sodium tetrahydroborate; lithium chloride / tetrahydrofuran; ethanol / 48 h / 0 - 20 °C

With pyridine; 1H-imidazole; sodium tetrahydroborate; N-Bromosuccinimide; formic acid; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium sulfate; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 2-hydroxyethanethiol; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; 1: |Pictet-Spengler Synthesis;

DOI:10.1055/s-0032-1316579

Reference yield:

3-hydroxy-4-methoxy-5-methylbenzaldehyde (209624-66-8) → (1R,3S)-2-chloroethyl 8-(benzyloxy)-1-[(R)-1-({(R)-1-[6-(benzyloxy)-7-{[(trifluoromethyl)sulfonyl]oxy}benzo[d][1,3]dioxol-4-yl]-2-hydroxyethyl}amino)-2-{(tert-butyldimethylsilyl)oxy}ethyl]-3-(dimethoxymethyl)-7-methoxy-6-methyl-3,4-dihydroisoquinoline-2(1H)-carboxylate (1414948-78-9)

Guidance literature:

Multi-step reaction with 21 steps

1.1: potassium carbonate / acetone / 2 h / 20 °C

2.1: N,N,N',N'-tetramethylguanidine / dichloromethane / 48 h / 20 °C

3.1: (+)-1,2-bis-[(2S,5S)-2,5-diethylphospholano]benzene (1,5-cycloctadiene)rhodium(I) trifluoromethanesulfonate; hydrogen / ethyl acetate / 72 h / 50 °C / 25858.1 Torr

4.1: methanol; acetyl chloride / 0 - 20 °C

5.1: triethylamine / dichloromethane / 0 - 20 °C

6.1: water; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C

7.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 24 h / 0 - 20 °C

8.1: diisobutylaluminium hydride / toluene / 1.5 h / -78 °C / Inert atmosphere

8.2: 1 h / 20 °C

9.1: water; toluene-4-sulfonic acid / methanol / 1.5 h / 20 °C / Reflux

10.1: 10% Pd/C; hydrogen / methanol / 48 h / 20 °C / 760.05 Torr

11.1: formic acid; sodium sulfate / dichloromethane / 24 h / 0 - 20 °C

12.1: potassium carbonate / acetone / 41.5 h / 0 - 20 °C

13.1: pyridine / dichloromethane / 1 h / 0 - 20 °C

14.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetonitrile / 2 h / 0 - 20 °C

15.1: N-ethyl-N,N-diisopropylamine / acetonitrile / 23.5 h / 0 - 20 °C

16.1: N-Bromosuccinimide / dichloromethane / 0.5 h / 0 °C

17.1: trifluoroacetic acid / dichloromethane / 0.42 h / 0 °C

18.1: pyridine / dichloromethane / 0.5 h / 0 °C

19.1: triethylamine / 1 h / 20 °C

20.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 0 - 20 °C

21.1: sodium tetrahydroborate; lithium chloride / tetrahydrofuran; ethanol / 48 h / 0 - 20 °C

With pyridine; 1H-imidazole; methanol; sodium tetrahydroborate; N-Bromosuccinimide; formic acid; (+)-1,2-bis-[(2S,5S)-2,5-diethylphospholano]benzene (1,5-cycloctadiene)rhodium(I) trifluoromethanesulfonate; 10% Pd/C; water; hydrogen; diisobutylaluminium hydride; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium sulfate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; trifluoroacetic acid; 2-hydroxyethanethiol; lithium chloride; lithium hydroxide; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 2.1: |Horner-Wadsworth-Emmons Olefination / 11.1: |Pictet-Spengler Synthesis;

DOI:10.1055/s-0032-1316579

upstream raw materials:

(S)-5-(2-amino-3,3-dimethoxypropyl)-2-methoxy-3-methylphenol

3-hydroxy-4-methoxy-5-methylbenzaldehyde

3-(benzyloxy)-4-methoxy-5-methylbenzaldehyde

(Z)-methyl 3-[3-(benzyloxy)-4-methoxy-5-methylphenyl]-2-[(tert-butoxycarbonyl)amino]acrylate

Downstream raw materials:

(3R,5R,6R,12S,12aS)-2-chloroethyl 7-(benzyloxy)-3-[6-(benzyloxy)-7-{[(trifluoromethyl)sulfonyl]oxy}benzo[d][1,3]dioxol-4-yl]-5-{[(tert-butyldimethylsilyl)oxy]methyl}-8-methoxy-9-methyl-3,5,6,11,12,12a-hexahydro-2H-6,12-epiminobenzo[e]oxazolo[3,2-a]azocine-13-carboxylate

(3R,5R,6R,12S,12aS)-2-chloroethyl 7-(benzyloxy)-3-[6-(benzyloxy)-7-methylbenzo[d][1,3]dioxol-4-yl]-5-{[(tert-butyldimethylsilyl)oxy]methyl}-8-methoxy-9-methyl-3,5,6,11,12,12a-hexahydro-2H-6,12-epiminobenzo[e]oxazolo[3,2-a]azocine-13-carboxylate

(3R,5R,6R,12S,12aS)-2,2,2-trichloroethyl 7-(benzyloxy)-3-[6-(benzyloxy)-7-methylbenzo[d][1,3]dioxol-4-yl]-5-{[(tert-butyldimethylsilyl)oxy]methyl}-8-methoxy-9-methyl-3,5,6,11,12,12a-hexahydro-2H-6,12-epiminobenzo[e]oxazolo[3,2-a]azocine-13-carboxylate

C₄₇H₅₇IN₂O₉Si

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