(R)-6-[(1E,7Z,9Z,11E)-(3R,4R,6R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-3-methyl-trideca-1,7,9,11-tetraenyl]-5,6-dihydro-pyran-2-one

Base Information

• Chemical Name: (R)-6-[(1E,7Z,9Z,11E)-(3R,4R,6R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-3-methyl-trideca-1,7,9,11-tetraenyl]-5,6-dihydro-pyran-2-one
• CAS No.: 343982-17-2
• Molecular Formula: C₄₇H₇₂O₆Si₃
• Molecular Weight: 817.342
• Mol file: 343982-17-2.mol

Synonyms:(R)-6-[(1E,7Z,9Z,11E)-(3R,4R,6R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-3-methyl-trideca-1,7,9,11-tetraenyl]-5,6-dihydro-pyran-2-one

Chemical Property of (R)-6-[(1E,7Z,9Z,11E)-(3R,4R,6R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-3-methyl-trideca-1,7,9,11-tetraenyl]-5,6-dihydro-pyran-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-6-[(1E,7Z,9Z,11E)-(3R,4R,6R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-3-methyl-trideca-1,7,9,11-tetraenyl]-5,6-dihydro-pyran-2-one

There total 43 articles about (R)-6-[(1E,7Z,9Z,11E)-(3R,4R,6R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-3-methyl-trideca-1,7,9,11-tetraenyl]-5,6-dihydro-pyran-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: 54.0%

t-butyldimethylsiyl triflate (69739-34-0) + (6R,1'E,3'R,4'R,6'R,7'Z,9'Z,11'E)-6-(6'-tert-butyldimethylsiloxy-13'-tert-butyldiphenylsiloxy-3',4'-dihydroxy-3'-methyl-1',7',9',11'-tridecatetraenyl)-5,6-dihydro-2H-pyran-2-one (343982-19-4) → (R)-6-[(1E,7Z,9Z,11E)-(3R,4R,6R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-3-methyl-trideca-1,7,9,11-tetraenyl]-5,6-dihydro-pyran-2-one (343982-17-2)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -20 ℃; for 3h;

DOI:10.1021/ja010195q

Reference yield: 40.0%

(R)-6-[(1E,7Z,9Z,11E)-(4R,6R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-3-methyl-trideca-1,7,9,11-tetraenyl]-5,6-dihydro-2H-pyran-2-ol → (R)-6-[(1E,7Z,9Z,11E)-(3S,4R,6R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-3-methyl-trideca-1,7,9,11-tetraenyl]-5,6-dihydro-pyran-2-one + (R)-6-[(1E,7Z,9Z,11E)-(3R,4R,6R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-3-methyl-trideca-1,7,9,11-tetraenyl]-5,6-dihydro-pyran-2-one (343982-17-2)

Guidance literature:

With silver carbonate; In benzene; at 80 ℃; for 2h;

DOI:10.1021/ja010195q

Reference yield:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) → (R)-6-[(1E,7Z,9Z,11E)-(3R,4R,6R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-3-methyl-trideca-1,7,9,11-tetraenyl]-5,6-dihydro-pyran-2-one (343982-17-2)

Guidance literature:

Multi-step reaction with 25 steps

1.1: 95 percent / BF₃*OEt₂ / cyclohexane; CH₂Cl₂ / 25 °C

2.1: DIBAL-H / CH₂Cl₂; toluene / 1.5 h / -78 °C

3.1: 73 percent / MsCl; Et₃N; DMAP / CH₂Cl₂ / 2.5 h / Heating

4.1: (DHQD)2AQN; K₂OsO₂(OH)4; K₃Fe(CN)6 / K₂CO₃; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 24 h / 2 °C

5.1: Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

6.1: 88 percent / KHMDS; 18-crown-6/MeCN complex / tetrahydrofuran; toluene / 2 h / 0 °C

7.1: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / -30 °C

8.1: 90 percent / DIBAL-H / toluene; hexane / 0.33 h / -20 °C

9.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

10.1: PPh₃ / CH₂Cl₂ / 0.08 h / 0 °C

10.2: 3.90 g / Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

11.1: 95 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 25 °C

12.1: 93 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 0.5 h / 25 °C

13.1: 84 percent / Bu₃SnH; (Ph₃P)4Pd / benzene / 2.5 h / 25 °C

14.1: 83 percent / iPr₂NEt; 1-methyl-2-pyrrolidinone; (CH₃CN)2PdCl₂ / 2 h / 25 °C

15.1: 98 percent / DIBAL-H / toluene / 0.08 h / -78 °C

16.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 25 °C

17.1: BuLi / toluene; hexane / 0.25 h / -78 °C

17.2: toluene; hexane / 0.25 h / -78 °C

18.1: 140 mg / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

19.1: 75 percent / t-BuOK / toluene; tetrahydrofuran / 2 h / 0 °C

20.1: CeCl₃; t-BuLi / tetrahydrofuran; diethyl ether / 0.17 h / -78 °C

20.2: tetrahydrofuran; diethyl ether; toluene / 0.08 h / -78 °C

21.1: PPTS / 2 h / 25 °C

22.1: Et₃N / DMAP / CH₂Cl₂ / 1 h

23.1: 2,6-lutidine / CH₂Cl₂ / 0.75 h / -20 °C

24.1: aq. HCl / acetone / 2 h / -15 - 0 °C

25.1: 40 percent / Ag₂CO₃-Celite / benzene / 2 h / 80 °C

With 2,6-dimethylpyridine; 1-methyl-pyrrolidin-2-one; hydrogenchloride; dmap; dichloro bis(acetonitrile) palladium(II); tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; cerium(III) chloride; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; 18-crown-6 ether; boron trifluoride diethyl etherate; potassium tert-butylate; tert.-butyl lithium; tri-n-butyl-tin hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; silver carbonate; acetonitrile; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); dmap; methanesulfonamide; pyridinium p-toluenesulfonate; potassium carbonate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; water; acetone; toluene; tert-butyl alcohol; benzene; 4.1: Sharpless assymetric dihydroxylation / 9.1: Dess-Martin oxidation / 10.1: Corey and Fuchs reaction / 14.1: Stille coupling / 15.1: Stille coupling / 16.1: Dess-Martin oxidation / 18.1: Dess-Martin oxidation;

DOI:10.1021/ja010195q

upstream raw materials:

t-butyldimethylsiyl triflate

(6R,1'E,3'R,4'R,6'R,7'Z,9'Z,11'E)-6-(6'-tert-butyldimethylsiloxy-13'-tert-butyldiphenylsiloxy-3',4'-dihydroxy-3'-methyl-1',7',9',11'-tridecatetraenyl)-5,6-dihydro-2H-pyran-2-one

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

(4R)-4-[(4-methoxybenzyl)oxymethyl]-γ-butyrolactone

Downstream raw materials:

(+)-fostriecin

phosphoric acid 3-(tert-butyl-dimethyl-silanyloxy)-1-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-allyl]-10-(tert-butyl-diphenyl-silanyloxy)-deca-4,6,8-trienyl ester bis-(4-methoxy-benzyl) ester