13-O-De(2,6-dideoxy-β-D-arabino-hexopyranosyl)venturicidin B

Base Information

• Chemical Name: 13-O-De(2,6-dideoxy-β-D-arabino-hexopyranosyl)venturicidin B
• CAS No.: 33538-64-6
• Molecular Formula: C₃₄H₅₆O₇
• Molecular Weight: 576.814
• Mol file: 33538-64-6.mol

Synonyms:4,21-Dioxabicyclo[15.3.1]heneicosa-9,15,18-trien-3-one,1,11-dihydroxy-5-(4-hydroxy-1,3,5-trimethyl-6-oxooctyl)-6,8,16,18-tetramethyl-,stereoisomer (8CI); Venturicidin B,13-O-de(2,6-dideoxy-b-D-arabino-hexopyranosyl)-;4,21-Dioxabicyclo[15.3.1]heneicosane, venturicidin B deriv.;4,21-Dioxabicyclo[15.3.1]heneicosa-9,15,18-trien-3-one,1,11-dihydroxy-5-(4-hydroxy-1,3,5-trimethyl-6-oxooctyl)-6,8,16,18-tetramethyl-,[1R-[1R*,5S*(1R*,3R*,4S*,5S*),6R*,8R*,9E,11R*,15E,17R*]]-; VenturicidinB aglycone; Venturicidin X

Chemical Property of 13-O-De(2,6-dideoxy-β-D-arabino-hexopyranosyl)venturicidin B

Chemical Property:

• PSA: 113.29000
• LogP: 6.06010

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 13-O-De(2,6-dideoxy-β-D-arabino-hexopyranosyl)venturicidin B

There total 38 articles about 13-O-De(2,6-dideoxy-β-D-arabino-hexopyranosyl)venturicidin 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:

(5R,6S)-6-((1R,3R)-1,3-Dimethyl-pent-4-enyl)-5-methyl-tetrahydro-pyran-2-one (129117-26-6) → Venturicidin X (33538-64-6)

Guidance literature:

Multi-step reaction with 14 steps

1: LDA / hexamethylphosphoric acid triamide / -78 °C

2: 1.) LiAlH₄ 2.) imidazole 3.) pyridine / 3.) HMPA

3: 1.) O₃/Me₂S

4: 1.) PPTS 2.) O₃/Me₂S 4.) PDC/Zeolite 3A

5: 1.) PPTS 2.) tetramethylammonium triacetoxyborohydride / 1.) MeOH

6: 93 percent / CSA

7: DIBAH

8: 1.) 2,4,6-trichlorobenzoyl chloride/Et₃N 2.) 2/DMAP

9: 68 percent / n-Bu₄NF*3H₂O

10: 1.) PDC/Zeolite 3A 2.) K₂CO₃/18-Crown-6 / 2.) toluene, r.t.

11: 43 percent / NaBH₄-CeCl₃

12: 1.) pyridine 2.) PPTS / 1.) DMAP 2.) MeOH

13: 44 percent / RuCl₂(PPh₃)3/K₂CO₃

14: 1.) K₂CO₃ 2.) AcOH/H₂O(4:1) / 1.) MeOH

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; tris(triphenylphosphine)ruthenium(II) chloride; cerium(III) chloride; 18-crown-6 ether; dimethylsulfide; Zeolite 3A; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; ozone; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/S0040-4039(00)88867-X

Reference yield:

(5R,6S)-6-((1R,3R)-1,3-Dimethyl-pent-4-enyl)-5-methyl-tetrahydro-pyran-2-one (129117-26-6) → (9E,15E)-(1R,5S,6R,8R,11S,17R)-1,11-Dihydroxy-5-((1R,3R,4S,5S)-4-hydroxy-1,3,5-trimethyl-6-oxo-octyl)-6,8,16,18-tetramethyl-4,21-dioxa-bicyclo[15.3.1]henicosa-9,15,18-trien-3-one (33538-64-6,106927-20-2)

Guidance literature:

Multi-step reaction with 14 steps

1: LDA / hexamethylphosphoric acid triamide / -78 °C

2: 1.) LiAlH₄ 2.) imidazole 3.) pyridine / 3.) HMPA

3: 1.) O₃/Me₂S

4: 1.) PPTS 2.) O₃/Me₂S 4.) PDC/Zeolite 3A

5: 1.) PPTS 2.) tetramethylammonium triacetoxyborohydride / 1.) MeOH

6: 93 percent / CSA

7: DIBAH

8: 1.) 2,4,6-trichlorobenzoyl chloride/Et₃N 2.) 2/DMAP

9: 68 percent / n-Bu₄NF*3H₂O

10: 1.) PDC/Zeolite 3A 2.) K₂CO₃/18-Crown-6 / 2.) toluene, r.t.

11: 55 percent / NaBH₄-CeCl₃

12: 1.) pyridine 2.) PPTS / 1.) DMAP 2.) MeOH

13: RuCl₂(PPh₃)3/K₂CO₃

14: 1.) K₂CO₃ 2.) AcOH/H₂O(4:1) / 1.) MeOH

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; tris(triphenylphosphine)ruthenium(II) chloride; cerium(III) chloride; 18-crown-6 ether; dimethylsulfide; Zeolite 3A; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; ozone; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/S0040-4039(00)88867-X

Reference yield:

tert-Butyl-[(1R,2R,4R)-1-((S)-2-iodo-1-methyl-ethyl)-2,4-dimethyl-hex-5-enyloxy]-dimethyl-silane (129117-24-4) → Venturicidin X (33538-64-6)

Guidance literature:

Multi-step reaction with 16 steps

1: 68 percent / LDA

2: 93 percent / CF₃COOH

3: LDA / hexamethylphosphoric acid triamide / -78 °C

4: 1.) LiAlH₄ 2.) imidazole 3.) pyridine / 3.) HMPA

5: 1.) O₃/Me₂S

6: 1.) PPTS 2.) O₃/Me₂S 4.) PDC/Zeolite 3A

7: 1.) PPTS 2.) tetramethylammonium triacetoxyborohydride / 1.) MeOH

8: 93 percent / CSA

9: DIBAH

10: 1.) 2,4,6-trichlorobenzoyl chloride/Et₃N 2.) 2/DMAP

11: 68 percent / n-Bu₄NF*3H₂O

12: 1.) PDC/Zeolite 3A 2.) K₂CO₃/18-Crown-6 / 2.) toluene, r.t.

13: 43 percent / NaBH₄-CeCl₃

14: 1.) pyridine 2.) PPTS / 1.) DMAP 2.) MeOH

15: 44 percent / RuCl₂(PPh₃)3/K₂CO₃

16: 1.) K₂CO₃ 2.) AcOH/H₂O(4:1) / 1.) MeOH

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; tris(triphenylphosphine)ruthenium(II) chloride; cerium(III) chloride; 18-crown-6 ether; dimethylsulfide; Zeolite 3A; 2,4,6-trichlorobenzoyl chloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; water; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; ozone; acetic acid; triethylamine; trifluoroacetic acid; tetramethylammonium triacetoxyborohydride; lithium diisopropyl amide; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1016/S0040-4039(00)88867-X

upstream raw materials:

Acetic acid (9E,15E)-(1R,5S,6R,8R,11R,17R)-5-((1R,3R,4S,5S)-4-hydroxy-1,3,5-trimethyl-6-oxo-octyl)-1-methoxy-6,8,16,18-tetramethyl-3-oxo-4,21-dioxa-bicyclo[15.3.1]henicosa-9,15,18-trien-11-yl ester

(5R,6S)-6-((1R,3R)-1,3-Dimethyl-pent-4-enyl)-5-methyl-tetrahydro-pyran-2-one

tert-Butyl-[(1R,2R,4R)-1-((S)-2-iodo-1-methyl-ethyl)-2,4-dimethyl-hex-5-enyloxy]-dimethyl-silane

(2R,3R,4R,6R)-3-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-oct-7-en-1-ol

Refernces

• 1、 Akita,Yamada,Matsukura,Nakata,Oishi. "Total synthesis of the aglycone of venturicidins A and B. II". . p. 1735 - 1738. Retrieved 2007/10/02.