torrubiellone B

Base Information

Chemical Name:torrubiellone B
CAS No.:1258948-58-1
Molecular Formula:C₂₂H₂₉NO₆
Molecular Weight:403.475
Hs Code.:

Synonyms:torrubiellone B

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Chemical Property of torrubiellone B

Chemical Property:

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Technology Process of torrubiellone B

There total 7 articles about torrubiellone B 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: 47.0%

: 1501971-56-7
(R,2E,4E,6E)-1-(5-((1s,4S)-4-(tert-butyldimethylsilyloxy)-1-hydroxycyclohexyl)-2,4-bis(methoxymethoxy)pyridin-3-yl)-8-(tert-butyldimethylsilyloxymethyl)deca-2,4,6-trien-1-one

: 1258948-58-1
torrubiellone B

Guidance literature:: With toluene-4-sulfonic acid; In tetrahydrofuran; hexane; water; at 20 ℃; for 12h;
DOI:10.1021/ol402820d

Reference yield:

: 626-03-9
4-hydroxy-2-pyridone

: 1258948-58-1
torrubiellone B

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

2.1: tert.-butyl lithium / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

3.1: sec.-butyllithium / tetrahydrofuran / 1 h / -60 °C / Inert atmosphere

3.2: 3 h / -60 - 20 °C / Inert atmosphere

4.1: Dess-Martin periodane; pyridine / dichloromethane / 3 h / 0 - 20 °C

5.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

5.2: 0 - 20 °C / Inert atmosphere

6.1: toluene-4-sulfonic acid / tetrahydrofuran; water; hexane / 12 h / 20 °C

With pyridine; tert.-butyl lithium; sec.-butyllithium; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol402820d

Reference yield:

: 645386-89-6
(R)-4-benzyl-3-((S)-2-(benzyloxymethyl)butanoyl)-1,3-oxazolidin-2-one

: 1258948-58-1
torrubiellone B

Guidance literature:: Multi-step reaction with 12 steps

1.1: hydrogen; palladium 10% on activated carbon / ethanol; dichloromethane / 23 h / 20 °C / Inert atmosphere

2.1: triethylamine; dmap / dichloromethane / 5.5 h / 0 - 20 °C / Inert atmosphere

3.1: lithium borohydride / methanol; diethyl ether / 2 h / -20 - 0 °C / Inert atmosphere

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C

4.2: -78 - 20 °C

5.1: dichloromethane / 20 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 °C / Inert atmosphere

7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C

7.2: -78 - 20 °C

8.1: dichloromethane / 20 °C / Inert atmosphere

9.1: diisobutylaluminium hydride / dichloromethane; hexane / 2 h / -78 °C / Inert atmosphere

10.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C

10.2: -78 - 20 °C

11.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

11.2: 0 - 20 °C / Inert atmosphere

12.1: toluene-4-sulfonic acid / tetrahydrofuran; water; hexane / 12 h / 20 °C

With dmap; lithium borohydride; oxalyl dichloride; palladium 10% on activated carbon; hydrogen; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; 4.1: |Swern Oxidation / 4.2: |Swern Oxidation / 5.1: |Wittig Olefination / 7.1: |Swern Oxidation / 7.2: |Swern Oxidation / 8.1: |Wittig Olefination / 10.1: |Swern Oxidation / 10.2: |Swern Oxidation;
DOI:10.1021/ol402820d