(3S,4R,5R)-4-(benzyloxy)-3-[3-(benzyloxy)propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2,5-methano-1H-2-benzazepine

Base Information

• Chemical Name: (3S,4R,5R)-4-(benzyloxy)-3-[3-(benzyloxy)propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2,5-methano-1H-2-benzazepine
• CAS No.: 1431116-72-1
• Molecular Formula: C₃₀H₃₅NO₄
• Molecular Weight: 473.612

Synonyms:(3S,4R,5R)-4-(benzyloxy)-3-[3-(benzyloxy)propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2,5-methano-1H-2-benzazepine

Chemical Property of (3S,4R,5R)-4-(benzyloxy)-3-[3-(benzyloxy)propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2,5-methano-1H-2-benzazepine

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (3S,4R,5R)-4-(benzyloxy)-3-[3-(benzyloxy)propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2,5-methano-1H-2-benzazepine

There total 21 articles about (3S,4R,5R)-4-(benzyloxy)-3-[3-(benzyloxy)propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2,5-methano-1H-2-benzazepine 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:

C30H37NO5 → (3S,4R,5R)-4-(benzyloxy)-3-[3-(benzyloxy)propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2,5-methano-1H-2-benzazepine (1431116-72-1)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In diethyl ether; acetonitrile; at 20 ℃; for 18h;

DOI:10.1016/j.tet.2013.03.012

Reference yield:

C23H31NO7S → (3S,4R,5R)-4-(benzyloxy)-3-[3-(benzyloxy)propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2,5-methano-1H-2-benzazepine (1431116-72-1)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 1H-imidazole / tetrahydrofuran / 24 h / 0 - 20 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C

3.1: potassium iodide; sodium hydride / tetrahydrofuran / 6 h / 60 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C

5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere

6.1: dichloromethane / 2 h / 20 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 78 °C / Inert atmosphere

8.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.5 h / -30 °C / Inert atmosphere

8.2: 15 h / -30 °C / Inert atmosphere

9.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere

10.1: dichloromethane / 2 h / 20 °C / Inert atmosphere

11.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 7 h / -30 - 20 °C / Inert atmosphere

12.1: ozone / methanol; dichloromethane / 2 h / -70 °C

13.1: sodium tetrahydroborate / methanol; dichloromethane / 23 h

14.1: triethylamine; dmap / dichloromethane / 14 h / 20 °C

15.1: sodium hydride / tetrahydrofuran / 17 h / 0 - 20 °C

16.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

17.1: naphthalene; sodium / 1,2-dimethoxyethane / -70 °C / Inert atmosphere

18.1: 1H-imidazole; triphenylphosphine; iodine / acetonitrile; diethyl ether / 18 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; naphthalene; L-(+)-diisopropyl tartrate; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; iodine; sodium; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; ozone; triethylamine; triphenylphosphine; potassium iodide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; toluene; acetonitrile; 5.1: |Dess-Martin Oxidation / 6.1: |Wittig Olefination / 9.1: |Dess-Martin Oxidation / 10.1: |Wittig Olefination;

DOI:10.1016/j.tet.2013.03.012

Reference yield:

C37H47NO6SSi (1431116-46-9) → (3S,4R,5R)-4-(benzyloxy)-3-[3-(benzyloxy)propyl]-1,3,4,5-tetrahydro-7,8-dimethoxy-2,5-methano-1H-2-benzazepine (1431116-72-1)

Guidance literature:

Multi-step reaction with 16 steps

1.1: potassium iodide; sodium hydride / tetrahydrofuran / 6 h / 60 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 3 h / 20 °C

3.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.1: dichloromethane / 2 h / 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / 78 °C / Inert atmosphere

6.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane / 0.5 h / -30 °C / Inert atmosphere

6.2: 15 h / -30 °C / Inert atmosphere

7.1: Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere

8.1: dichloromethane / 2 h / 20 °C / Inert atmosphere

9.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 7 h / -30 - 20 °C / Inert atmosphere

10.1: ozone / methanol; dichloromethane / 2 h / -70 °C

11.1: sodium tetrahydroborate / methanol; dichloromethane / 23 h

12.1: triethylamine; dmap / dichloromethane / 14 h / 20 °C

13.1: sodium hydride / tetrahydrofuran / 17 h / 0 - 20 °C

14.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C

15.1: naphthalene; sodium / 1,2-dimethoxyethane / -70 °C / Inert atmosphere

16.1: 1H-imidazole; triphenylphosphine; iodine / acetonitrile; diethyl ether / 18 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; dmap; sodium tetrahydroborate; naphthalene; L-(+)-diisopropyl tartrate; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; iodine; sodium; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; ozone; triethylamine; triphenylphosphine; potassium iodide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; toluene; acetonitrile; 3.1: |Dess-Martin Oxidation / 4.1: |Wittig Olefination / 7.1: |Dess-Martin Oxidation / 8.1: |Wittig Olefination;

DOI:10.1016/j.tet.2013.03.012

upstream raw materials:

C₃₇H₄₇NO₆SSi

C₂₈H₃₅NO₆S

C₃₁H₃₇NO₇S

N-(3,4-dimethoxybenzyl)-4-methylbenzenesulfonamide

Downstream raw materials:

C₃₂H₄₁NO₄Si

(3S,4R,5R)-3-[3-(tert-butyldiphenylsilyloxy)propyl]-7,8-dimethoxy-1,3,4,5-tetrahydro-2,5-methano-1H-2-benzazepin-4-yl acetate

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