(1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-5-Ethyl-6,7,9,12-tetrahydroxy-2,6,8,10,12,17-hexamethyl-15-phenyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one

Base Information

• Chemical Name: (1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-5-Ethyl-6,7,9,12-tetrahydroxy-2,6,8,10,12,17-hexamethyl-15-phenyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one
• CAS No.: 105545-15-1
• Molecular Formula: C₂₈H₄₄O₈
• Molecular Weight: 508.653
• Mol file: 105545-15-1.mol

Synonyms:

Chemical Property of (1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-5-Ethyl-6,7,9,12-tetrahydroxy-2,6,8,10,12,17-hexamethyl-15-phenyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-5-Ethyl-6,7,9,12-tetrahydroxy-2,6,8,10,12,17-hexamethyl-15-phenyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one

There total 58 articles about (1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-5-Ethyl-6,7,9,12-tetrahydroxy-2,6,8,10,12,17-hexamethyl-15-phenyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-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: 80.0%

benzaldehyde dimethyl acetal (1125-88-8) + 9S-Dihydroerythronolide A aglycon (15562-19-3,28316-68-9) → (1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-5-Ethyl-6,7,9,12-tetrahydroxy-2,6,8,10,12,17-hexamethyl-15-phenyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one (105545-15-1,124990-94-9)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 0 ℃; for 24h;

DOI:10.1016/S0040-4039(00)84383-X

Reference yield:

5-O-benzyl-1,6,7-trideoxy-3,4-O-isopropylidene-4-C-methyl-keto-D-arabino-2-heptulose (105544-93-2) → (1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-5-Ethyl-6,7,9,12-tetrahydroxy-2,6,8,10,12,17-hexamethyl-15-phenyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one (105545-15-1,124990-94-9)

Guidance literature:

Multi-step reaction with 17 steps

1: 1.) NH₂NH₂xH₂O, Et₃N, 2.) I₂, 1,1,3,3-tetramethylquanidine / 1.) ethanol, 70 deg C, 1 h, 2.) toluene, 0 deg C, 0.5 h

2: butyllithium / diethyl ether; hexane / 1 h / -100 °C

3: H₂, ClRh(PPh₃)3 / benzene / 120 h / 24 °C / 36775.4 Torr

4: 95 percent / 46percent aqueous / HF / acetonitrile / 1 h / 24 °C

5: KOH / dimethylformamide / 5 h / 24 °C

6: 93 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 23 °C

7: 92 percent / H₂ / palladium black / ethanol / 0.5 h / 20 °C

8: 82 percent / imidazole / dimethylformamide / 3 h / 25 °C

9: 85 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / 25 °C

10: 86 percent / 4-dimethylaminopyridine / pyridine / 20 h / 60 °C

11: 81 percent / tetrabutylammonium fluoride / tetrahydrofuran / 8 h / 60 °C

12: 85 percent / pyridinium dichromate, molecular sieves 3A / CH₂Cl₂ / 4 h / 22 °C

13: 96 percent / aqueous NaOH / dioxane / 2 h / 23 °C

14: 95 percent / triphenylphosphine / tetrahydrofuran / 8 h / 22 °C

15: 65 percent / toluene / 14 h / 110 °C

16: acetic acid / H₂O / 4 h / 24 °C

17: 80 percent / 10-campphorsulfonic acid / CH₂Cl₂ / 24 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; potassium hydroxide; sodium hydroxide; Wilkinson's catalyst; dipyridinium dichromate; n-butyllithium; 3 A molecular sieve; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; iodine; pyridinium p-toluenesulfonate; hydrazine hydrate; acetic acid; triethylamine; triphenylphosphine; N,N,N',N'-tetramethylguanidine; hydrogen fluoride; palladium; In tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;

DOI:10.1246/bcsj.62.2618

Reference yield:

3-O-benzyl-1,2-dideoxy-4,5-isopropylidene-4-methyl-D-manno-heptitol (105544-92-1) → (1S,2R,5R,6S,7R,8S,9S,10R,12R,13R,17S)-5-Ethyl-6,7,9,12-tetrahydroxy-2,6,8,10,12,17-hexamethyl-15-phenyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecan-3-one (105545-15-1,124990-94-9)

Guidance literature:

Multi-step reaction with 20 steps

1: NaIO₄ / acetone; H₂O / 3 h

2: 90.6 percent / magnesium powder / diethyl ether / 2 h / 27 °C

3: 98 percent / PCC, molecular sieves 3A / CH₂Cl₂ / 1.5 h / 25 °C

4: 1.) NH₂NH₂xH₂O, Et₃N, 2.) I₂, 1,1,3,3-tetramethylquanidine / 1.) ethanol, 70 deg C, 1 h, 2.) toluene, 0 deg C, 0.5 h

5: butyllithium / diethyl ether; hexane / 1 h / -100 °C

6: H₂, ClRh(PPh₃)3 / benzene / 120 h / 24 °C / 36775.4 Torr

7: 95 percent / 46percent aqueous / HF / acetonitrile / 1 h / 24 °C

8: KOH / dimethylformamide / 5 h / 24 °C

9: 93 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 23 °C

10: 92 percent / H₂ / palladium black / ethanol / 0.5 h / 20 °C

11: 82 percent / imidazole / dimethylformamide / 3 h / 25 °C

12: 85 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / 25 °C

13: 86 percent / 4-dimethylaminopyridine / pyridine / 20 h / 60 °C

14: 81 percent / tetrabutylammonium fluoride / tetrahydrofuran / 8 h / 60 °C

15: 85 percent / pyridinium dichromate, molecular sieves 3A / CH₂Cl₂ / 4 h / 22 °C

16: 96 percent / aqueous NaOH / dioxane / 2 h / 23 °C

17: 95 percent / triphenylphosphine / tetrahydrofuran / 8 h / 22 °C

18: 65 percent / toluene / 14 h / 110 °C

19: acetic acid / H₂O / 4 h / 24 °C

20: 80 percent / 10-campphorsulfonic acid / CH₂Cl₂ / 24 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; potassium hydroxide; sodium hydroxide; sodium periodate; Wilkinson's catalyst; dipyridinium dichromate; n-butyllithium; 3 A molecular sieve; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; hydrogen; iodine; pyridinium p-toluenesulfonate; hydrazine hydrate; magnesium; acetic acid; triethylamine; triphenylphosphine; pyridinium chlorochromate; N,N,N',N'-tetramethylguanidine; hydrogen fluoride; palladium; In tetrahydrofuran; 1,4-dioxane; pyridine; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;

DOI:10.1246/bcsj.62.2618

upstream raw materials:

(diethoxymethyl)benzene

9S-Dihydroerythronolide A aglycon

benzaldehyde dimethyl acetal

3,5:9,11-di-O-isopropylidene.(9S)-9-deoxo-hydroxyerythronolide

Downstream raw materials:

erythronolide A

(1S,2R,5R,6S,7R,8R,10R,12R,13R,17S)-5-Ethyl-6,7,12-trihydroxy-2,6,8,10,12,17-hexamethyl-15-phenyl-4,14,16-trioxa-bicyclo[11.3.1]heptadecane-3,9-dione

Refernces

• 1、 Kochetkov, N. K.,Sviridov, A. F.,Ermolenko, M. S.,Yashunsky, D. V.,Borodkin, V. S.. "STEREO-CONTROLLED SYNTHESIS OF ERYTHRONOLIDES A AND B FROM 1,6-ANHYDRO-β-D-GLUCOPYRANOSE (LEVOGLUCOSAN). SKELETON ASSEMBLY IN (C9 - C13) + (C7 - C8) + (C1 - C6) SEQUENCE". . p. 5109 - 5136. Retrieved 2007/10/02.