Carbonic acid allyl ester (1R,2R,5R,6S)-1-methyl-4-oxo-2-((1E,3E,7E,9E)-(5R,11S)-5,7,11-trimethyl-trideca-1,3,7,9-tetraenyl)-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester

Base Information

• Chemical Name: Carbonic acid allyl ester (1R,2R,5R,6S)-1-methyl-4-oxo-2-((1E,3E,7E,9E)-(5R,11S)-5,7,11-trimethyl-trideca-1,3,7,9-tetraenyl)-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester
• CAS No.: 359766-34-0
• Molecular Formula: C₂₆H₃₆O₆
• Molecular Weight: 444.568
• Mol file: 359766-34-0.mol

Synonyms:

Chemical Property of Carbonic acid allyl ester (1R,2R,5R,6S)-1-methyl-4-oxo-2-((1E,3E,7E,9E)-(5R,11S)-5,7,11-trimethyl-trideca-1,3,7,9-tetraenyl)-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbonic acid allyl ester (1R,2R,5R,6S)-1-methyl-4-oxo-2-((1E,3E,7E,9E)-(5R,11S)-5,7,11-trimethyl-trideca-1,3,7,9-tetraenyl)-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester

There total 26 articles about Carbonic acid allyl ester (1R,2R,5R,6S)-1-methyl-4-oxo-2-((1E,3E,7E,9E)-(5R,11S)-5,7,11-trimethyl-trideca-1,3,7,9-tetraenyl)-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester 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: 88.0%

Carbonic acid allyl ester (1R,2R,5R,6S)-4-hydroxy-1-methyl-2-((1E,3E,7E,9E)-(5R,11S)-5,7,11-trimethyl-trideca-1,3,7,9-tetraenyl)-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester → Carbonic acid allyl ester (1R,2R,5R,6S)-1-methyl-4-oxo-2-((1E,3E,7E,9E)-(5R,11S)-5,7,11-trimethyl-trideca-1,3,7,9-tetraenyl)-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester (359766-34-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 0.25h;

DOI:10.1021/ol010089t

Reference yield:

benzyl 4,6-O-(phenylmethylene)-α-D-glucopyranoside (79549-73-8) → Carbonic acid allyl ester (1R,2R,5R,6S)-1-methyl-4-oxo-2-((1E,3E,7E,9E)-(5R,11S)-5,7,11-trimethyl-trideca-1,3,7,9-tetraenyl)-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester (359766-34-0)

Guidance literature:

Multi-step reaction with 23 steps

1.1: 100 percent / sodium hydride / dimethylformamide / 0.5 h / 20 °C

2.1: 93 percent / sodium cyanoborohydride; HCl; 3 Angstroem molecular sieve / tetrahydrofuran; diethyl ether / 0.17 h

3.1: 100 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

4.1: 66 percent / diethyl ether / 0.5 h / -78 °C

5.1: 100 percent / p-toluenesulfonic acid monohydrate / Pd/C / methanol; H₂O / 12 h / 70 °C

6.1: dibuthyltin oxide / benzene; methanol / 12 h / 70 °C

6.2: 100 percent / Et₃N / dioxane / 0.5 h / 20 °C

7.1: 94 percent / N-ethyl-diisopropylamine / CH₂Cl₂ / 0.5 h

8.1: 100 percent / H₂ / Pd(OH)2 / ethanol / 24 h / 20 °C / 760.05 Torr

9.1: 99 percent / diisopropylethylamine / dimethylformamide / 0.75 h / 20 °C

10.1: 75 percent / 2,6-lutidine / CH₂Cl₂ / 24 h / 20 °C

11.1: 95 percent / Bu₄NF; BF₃*OEt₂ / acetonitrile; tetrahydrofuran / 1 h / 20 °C

12.1: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

13.1: 90 percent / diisopropylethylamine; LiCl / acetonitrile / 1 h / 0 °C

14.1: 100 percent / NaBH₄ / Pd(PPh₃)4 / ethanol / 0.5 h / 20 °C

15.1: ClCO₂Me; Et₃N / tetrahydrofuran / 1 h / 0 °C

15.2: 71 percent / LiAlH(t-BuO)3; 4 Angstroem molecular sieve / tetrahydrofuran / 1 h / 20 °C

16.1: 100 percent / Bu₃P; DEAD / tetrahydrofuran / 0.5 h / 0 °C

17.1: 96 percent / H₂O₂; Mo₇O₂₄(NH₄)6*4H₂O / ethanol; H₂O / 8 h / 20 °C

18.1: 79 percent / KHMDS / tetrahydrofuran / 2 h / 20 °C

19.1: 99 percent / NaH / tetrahydrofuran / 0.5 h / 0 °C

20.1: 95 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C

21.1: 93 percent / 4-dimethylaminopyridine / pyridine / 24 h

22.1: 88 percent / HF*pyridine / tetrahydrofuran / 24 h / 20 °C

23.1: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.25 h

With 2,6-dimethylpyridine; hydrogenchloride; dmap; sodium tetrahydroborate; ammonium molybdate tetrahydrate; tributylphosphine; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; Dess-Martin periodane; toluene-4-sulfonic acid; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; methyl chloroformate; lithium chloride; diethylazodicarboxylate; palladium dihydroxide; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene; 13.1: Horner-Wadsworth-Emmons reaction / 16.1: Mitsunobu reaction / 18.1: Julia olefination;

DOI:10.1021/ol010089t

Reference yield:

(2R,3S,4R,5R,6S)-6-Benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3,4,5-triol (345342-62-3) → Carbonic acid allyl ester (1R,2R,5R,6S)-1-methyl-4-oxo-2-((1E,3E,7E,9E)-(5R,11S)-5,7,11-trimethyl-trideca-1,3,7,9-tetraenyl)-3,7-dioxa-bicyclo[4.1.0]hept-5-yl ester (359766-34-0)

Guidance literature:

Multi-step reaction with 18 steps

1.1: dibuthyltin oxide / benzene; methanol / 12 h / 70 °C

1.2: 100 percent / Et₃N / dioxane / 0.5 h / 20 °C

2.1: 94 percent / N-ethyl-diisopropylamine / CH₂Cl₂ / 0.5 h

3.1: 100 percent / H₂ / Pd(OH)2 / ethanol / 24 h / 20 °C / 760.05 Torr

4.1: 99 percent / diisopropylethylamine / dimethylformamide / 0.75 h / 20 °C

5.1: 75 percent / 2,6-lutidine / CH₂Cl₂ / 24 h / 20 °C

6.1: 95 percent / Bu₄NF; BF₃*OEt₂ / acetonitrile; tetrahydrofuran / 1 h / 20 °C

7.1: 83 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h

8.1: 90 percent / diisopropylethylamine; LiCl / acetonitrile / 1 h / 0 °C

9.1: 100 percent / NaBH₄ / Pd(PPh₃)4 / ethanol / 0.5 h / 20 °C

10.1: ClCO₂Me; Et₃N / tetrahydrofuran / 1 h / 0 °C

10.2: 71 percent / LiAlH(t-BuO)3; 4 Angstroem molecular sieve / tetrahydrofuran / 1 h / 20 °C

11.1: 100 percent / Bu₃P; DEAD / tetrahydrofuran / 0.5 h / 0 °C

12.1: 96 percent / H₂O₂; Mo₇O₂₄(NH₄)6*4H₂O / ethanol; H₂O / 8 h / 20 °C

13.1: 79 percent / KHMDS / tetrahydrofuran / 2 h / 20 °C

14.1: 99 percent / NaH / tetrahydrofuran / 0.5 h / 0 °C

15.1: 95 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C

16.1: 93 percent / 4-dimethylaminopyridine / pyridine / 24 h

17.1: 88 percent / HF*pyridine / tetrahydrofuran / 24 h / 20 °C

18.1: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.25 h

With 2,6-dimethylpyridine; dmap; sodium tetrahydroborate; ammonium molybdate tetrahydrate; tributylphosphine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; dihydrogen peroxide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; methyl chloroformate; lithium chloride; diethylazodicarboxylate; palladium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pyridine; methanol; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene; 8.1: Horner-Wadsworth-Emmons reaction / 11.1: Mitsunobu reaction / 13.1: Julia olefination;

DOI:10.1021/ol010089t

upstream raw materials:

benzyl 4,6-O-(phenylmethylene)-α-D-glucopyranoside

(2R,3S,4R,5R,6S)-6-Benzyloxy-2-benzyloxymethyl-3-methyl-tetrahydro-pyran-3,4,5-triol

(2R,4R,5R,6S)-4,5-Bis-allyloxy-6-benzyloxy-2-benzyloxymethyl-dihydro-pyran-3-one

(2R,4aR,6S,7R,8S,8aR)-7,8-Bis-allyloxy-6-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Downstream raw materials:

nafuredin