(-)-Grahamimycin A

Base Information

Chemical Name:(-)-Grahamimycin A
CAS No.:50376-39-1
Molecular Formula:C14H18O6
Molecular Weight:282.29
Hs Code.:
Mol file:50376-39-1.mol

Synonyms:(6R,12R,14R)-(3E,9E)-12-hydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8,11-trione;(3E,9E)-(6R,12R,14R)-12-Hydroxy-6,14-dimethyl-1,7-dioxa-cyclotetradeca-3,9-diene-2,8,11-trione;grahamimycin A;6R,12R,14R-colletoketol;

Suppliers and Price of (-)-Grahamimycin A

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 3 raw suppliers

Chemical Property of (-)-Grahamimycin A

Chemical Property:

PSA：89.90000
LogP:0.68600

Purity/Quality:: 99% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (-)-Grahamimycin A

There total 26 articles about (-)-Grahamimycin A 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: 87.0%

: 307298-69-7
(3E,6R,8R,11E,14R)-8,14-dimethyl-6-methoxymethyloxy-1,9-dioxacyclotetradeca-3,11-diene

: 50376-39-1,76023-57-9
(6R,12R,14R)-(3E,9E)-12-hydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8,11-trione

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 3 ℃; for 17h;
DOI:10.1021/jo000762c

Reference yield: 76.0%

: 21142-67-6
colletodiol

: 50376-39-1,76023-57-9
(6R,12R,14R)-(3E,9E)-12-hydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8,11-trione

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; toluene-4-sulfonic acid; In dichloromethane; for 5h;
DOI:10.1021/ol0269502

Reference yield:

: (7R)-7-hydroxy-octa-2,4-dienoic acid methyl ester

: 50376-39-1,76023-57-9
(6R,12R,14R)-(3E,9E)-12-hydroxy-6,14-dimethyl-1,7-dioxacyclotetradeca-3,9-diene-2,8,11-trione

Guidance literature:: Multi-step reaction with 9 steps

1.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 48 h

2.1: 71 percent / CH₃SO₂NH₂; K₂CO₃; K₃Fe(CN)6 / OsO₄; (DHQD)2PHAL / 2-methyl-propan-2-ol; H₂O / 0 °C

3.1: PPTS / methanol / 24 h

3.2: 88 percent / p-TsOH / methanol / 12 h

4.1: Et₃N; trichlorobenzoyl chloride / tetrahydrofuran / 3 h

4.2: 77 percent / DMAP / toluene / 2 h / 90 °C

5.1: 79 percent / TBAF; benzoic acid / tetrahydrofuran / 48 h

6.1: 79 percent / LiOH / tetrahydrofuran; H₂O / 6 h

7.1: 72 percent / DCC; DMAP; DMAP*HCl / CH₂Cl₂ / 12 h

8.1: 86 percent / Dowex 50W-8H⁽¹⁺⁾ resin / methanol / 6 h / Heating

9.1: 76 percent / TEMPO; p-TsOH / CH₂Cl₂ / 5 h

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; methanesulfonamide; Dowex 50W-8H⁽¹⁺⁾ resin; trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; 4-(dimethylamino)pyridine hydrochloride; pyridinium p-toluenesulfonate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; benzoic acid; potassium hexacyanoferrate(III); osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; 2.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ol0269502