tert-butyl (5-((4R,7S,8S,E)-7,8-bis(benzyloxy)-4-ethyl-10-methylundeca-5,9-dienoyl)-1,4,6-trimethoxy-7-methylnaphthalen-2-yl)carbamate

Base Information

Chemical Name:tert-butyl (5-((4R,7S,8S,E)-7,8-bis(benzyloxy)-4-ethyl-10-methylundeca-5,9-dienoyl)-1,4,6-trimethoxy-7-methylnaphthalen-2-yl)carbamate
CAS No.:1428860-05-2
Molecular Formula:C₄₇H₅₉NO₈
Molecular Weight:765.987
Hs Code.:

Synonyms:tert-butyl (5-((4R,7S,8S,E)-7,8-bis(benzyloxy)-4-ethyl-10-methylundeca-5,9-dienoyl)-1,4,6-trimethoxy-7-methylnaphthalen-2-yl)carbamate

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Chemical Property of tert-butyl (5-((4R,7S,8S,E)-7,8-bis(benzyloxy)-4-ethyl-10-methylundeca-5,9-dienoyl)-1,4,6-trimethoxy-7-methylnaphthalen-2-yl)carbamate

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Technology Process of tert-butyl (5-((4R,7S,8S,E)-7,8-bis(benzyloxy)-4-ethyl-10-methylundeca-5,9-dienoyl)-1,4,6-trimethoxy-7-methylnaphthalen-2-yl)carbamate

There total 8 articles about tert-butyl (5-((4R,7S,8S,E)-7,8-bis(benzyloxy)-4-ethyl-10-methylundeca-5,9-dienoyl)-1,4,6-trimethoxy-7-methylnaphthalen-2-yl)carbamate 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: 81.0%

: tert-butyl (5-((4R,7S,8S,E)-7,8-bis(benzyloxy)-4-ethyl-1-hydroxy-10-methylundeca-5,9-dien-1-yl)-1,4,6-trimethoxy-7-methylnaphthalen-2-yl)carbamate

: 1428860-05-2
tert-butyl (5-((4R,7S,8S,E)-7,8-bis(benzyloxy)-4-ethyl-10-methylundeca-5,9-dienoyl)-1,4,6-trimethoxy-7-methylnaphthalen-2-yl)carbamate

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.0833333h;
DOI:10.1021/ol400528g

Reference yield:

: C₂₂H₂₆O₄

: 1428860-05-2
tert-butyl (5-((4R,7S,8S,E)-7,8-bis(benzyloxy)-4-ethyl-10-methylundeca-5,9-dienoyl)-1,4,6-trimethoxy-7-methylnaphthalen-2-yl)carbamate

Guidance literature:: Multi-step reaction with 8 steps

1.1: n-butyllithium / tetrahydrofuran / 1 h / 0 - 20 °C

1.2: 20 h / -78 - 20 °C

2.1: propionic acid / 3 h / 125 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C

4.1: triphenylphosphine; 1H-imidazole; iodine / dichloromethane / 2 h / 20 °C

5.1: sodium cyanide / N,N-dimethyl-formamide / 12 h / 20 °C

6.1: diisobutylaluminium hydride / dichloromethane; hexane / 1 h / -78 °C

7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C

7.2: 3.08 h / -78 °C

8.1: pyridine; Dess-Martin periodane / dichloromethane / 0.08 h / 20 °C

With pyridine; 1H-imidazole; sodium cyanide; lithium aluminium tetrahydride; n-butyllithium; iodine; diisobutylaluminium hydride; Dess-Martin periodane; propionic acid; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: |Wittig Olefination / 1.2: |Wittig Olefination / 4.1: |Appel Halogenation;
DOI:10.1021/ol400528g

Reference yield:

: 1428860-02-9
(4R,7S,8S,E)-7,8-bis(benzyloxy)-4-ethyl-10-methylundeca-5,9-dienal

: 1428860-05-2
tert-butyl (5-((4R,7S,8S,E)-7,8-bis(benzyloxy)-4-ethyl-10-methylundeca-5,9-dienoyl)-1,4,6-trimethoxy-7-methylnaphthalen-2-yl)carbamate

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C

1.2: 3.08 h / -78 °C

2.1: pyridine; Dess-Martin periodane / dichloromethane / 0.08 h / 20 °C

With pyridine; n-butyllithium; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ol400528g