(9S,10S,12S,13S,14Z,19S,20R)-9,10,12,13-tetrahydroxy-4,19-dimethyl-20-{(2R,3S)-3-[(1S)-1-methylbutyl]oxiran-2-yl}-8,11,17-trimethylideneoxacycloicosa-3,5,14-trien-2-one

Base Information

• Chemical Name: (9S,10S,12S,13S,14Z,19S,20R)-9,10,12,13-tetrahydroxy-4,19-dimethyl-20-{(2R,3S)-3-[(1S)-1-methylbutyl]oxiran-2-yl}-8,11,17-trimethylideneoxacycloicosa-3,5,14-trien-2-one
• CAS No.: 424828-97-7
• Molecular Formula: C₃₁H₄₆O₇
• Molecular Weight: 530.702
• Mol file: 424828-97-7.mol

Synonyms:

Chemical Property of (9S,10S,12S,13S,14Z,19S,20R)-9,10,12,13-tetrahydroxy-4,19-dimethyl-20-{(2R,3S)-3-[(1S)-1-methylbutyl]oxiran-2-yl}-8,11,17-trimethylideneoxacycloicosa-3,5,14-trien-2-one

Chemical Property:

• Vapor Pressure: 4.51E-23mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (9S,10S,12S,13S,14Z,19S,20R)-9,10,12,13-tetrahydroxy-4,19-dimethyl-20-{(2R,3S)-3-[(1S)-1-methylbutyl]oxiran-2-yl}-8,11,17-trimethylideneoxacycloicosa-3,5,14-trien-2-one

There total 60 articles about (9S,10S,12S,13S,14Z,19S,20R)-9,10,12,13-tetrahydroxy-4,19-dimethyl-20-{(2R,3S)-3-[(1S)-1-methylbutyl]oxiran-2-yl}-8,11,17-trimethylideneoxacycloicosa-3,5,14-trien-2-one 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: 61.0%

C41H58O7 (476453-09-5) → (+)-amphidinolide A (476452-69-4,424828-97-7)

Guidance literature:

With amberlyst-15; In 1,4-dioxane; water; at 60 - 85 ℃; for 66h;

DOI:10.1021/ja053365y

Reference yield: 33.0%

(5S)-4,5-anhydro-1,2-dideoxy-5-[(1R)-1-methylbutyl]-2-prop-2-yn-1-yl-3-O-[(2E,4E,8R,9R,11S,12S)-8,9,11,12-tetrahydroxy-3-methyl-7,10-bis(methylene)pentadeca-2,4,14-trienoyl]-D-ribitol (692734-52-4) → (+)-amphidinolide A (424828-97-7)

Guidance literature:

With tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate; In 1,2-dichloro-ethane; at 50 ℃; for 6h;

DOI:10.1021/ja049292k

Reference yield:

(E)-5-(tert-Butyl-dimethyl-silanyloxy)-1-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-1,4-dioxa-spiro[4.4]non-2-yl]-pent-2-en-1-one (692734-53-5) → (+)-amphidinolide A (424828-97-7)

Guidance literature:

Multi-step reaction with 16 steps

1.1: K₃Fe(CN)6; K₂CO₃; methanesulfonamide / (DHQ)2-PHAL; aq. K₂OsO₄ / 2-methyl-propan-2-ol / 22 h / 0 °C

2.1: TsOH*H₂O / CH₂Cl₂ / 2 h / 0 °C

3.1: NaHMDS / tetrahydrofuran / 0 - 20 °C

3.2: 6.351 g / tetrahydrofuran / 11 h / 0 °C

4.1: 78 percent / TBAF / tetrahydrofuran / 24 h / 20 °C

5.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

6.2: 3.990 g / tetrahydrofuran; hexane / 15 h / 0 - 20 °C

7.1: 98 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

8.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

9.1: K₂CO₃ / methanol / 0.5 h / 0 °C

9.2: 86 mg / methanol / 25 h / 0 - 20 °C

10.1: 23 percent / Cp*Ru(MeCN)3PF₆ / 1,2-dichloro-ethane / 1 h / 50 °C

11.1: 88 percent / piperidine / CH₂Cl₂ / 3 h / 20 °C

12.1: aq. acetic acid / 20 h / 40 °C

13.1: 106 mg / i-Pr₂NEt / tetrahydrofuran / 0.17 h / 0 °C

14.1: ethoxyacetylene; [RuCl₂(p-cymene)]2 / toluene; hexane / 2 h / 20 °C

14.2: 51 percent / CSA / toluene; hexane; 1,2-dichloro-ethane / 2 h / 20 °C

15.1: 79 percent / TBAF; acetic acid / tetrahydrofuran / 30 h / 20 °C

16.1: 33 percent / Cp*Ry(MeCN)3PF₆ / 1,2-dichloro-ethane / 6 h / 50 °C

With piperidine; n-butyllithium; oxalyl dichloride; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; tris(acetonitrile)pentamethylcyclopentadienylruthenium(II) hexafluorophosphate; methanesulfonamide; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; potassium carbonate; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 1-ethoxyacetylene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); potassium osmate(VI); (DHQ)2-PHAL; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; toluene; tert-butyl alcohol; 5.1: Swern oxidation / 8.1: Swern oxidation;

DOI:10.1021/ja049292k

upstream raw materials:

C₄₁H₅₈O₇

(1S,2R)-2-Methyl-1-[(2R,3R)-3-((R)-1-methyl-butyl)-oxiranyl]-pent-4-yn-1-ol

C₂₁H₂₈O₄

(2E,4E)-7-((2R,3R)-3-{1-[(2R,3R)-3-allyl-1,4-dioxaspiro[4.4]non-2-yl]vinyl}-1,4-dioxaspiro[4.4]non-2-yl)-3-methylocta-2,4,7-trienoic acid