(2R)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-hydroxy-2-methylpropanoic acid

Base Information

• Chemical Name: (2R)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-hydroxy-2-methylpropanoic acid
• CAS No.: 1335029-06-5
• Molecular Formula: C₆₅H₈₆O₁₃
• Molecular Weight: 1075.39
• Mol file: 1335029-06-5.mol

Synonyms:

Chemical Property of (2R)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-hydroxy-2-methylpropanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-hydroxy-2-methylpropanoic acid

There total 40 articles about (2R)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-hydroxy-2-methylpropanoic acid 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:

C65H86O12 → (2R)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-hydroxy-2-methylpropanoic acid (1335029-06-5)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 0 ℃; for 1h;

DOI:10.1002/anie.201101741

Reference yield:

(S)-2-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)propan-1-ol (1039455-95-2) → (2R)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-hydroxy-2-methylpropanoic acid (1335029-06-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: carbon tetrabromide; triethylamine; triphenylphosphine / dichloromethane / 16 h

2.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 - 25 °C

2.2: 0.5 h / -78 °C

2.3: -78 - 25 °C

3.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C

3.2: 16 h / 0 - 20 °C

4.1: pyridine; sodium periodate; osmium(VIII) oxide / tetrahydrofuran; water / 2 h

5.1: tert.-butyl lithium / tetrahydrofuran; pentane / 0.75 h / -78 °C / Inert atmosphere

5.2: 0.75 h / -78 °C / Inert atmosphere

5.3: -78 - 20 °C / Inert atmosphere

6.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.75 h / 20 °C

7.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 0.17 h

7.2: 20.17 h

8.1: borane-THF; ethane / tetrahydrofuran; toluene / 0.12 h / 0 °C / Inert atmosphere

8.2: 0 - 20 °C / Inert atmosphere

9.1: water; acetic acid / tetrahydrofuran / 40 h / 55 °C

10.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h

11.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 1 h / 0 °C

With pyridine; sodium chlorite; sodium periodate; osmium(VIII) oxide; sodium dihydrogenphosphate dihydrate; borane-THF; 2-methyl-but-2-ene; ethane; carbon tetrabromide; water; tert.-butyl lithium; sulfur trioxide pyridine complex; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; acetonitrile; mineral oil; tert-butyl alcohol; pentane; 7.1: Horner-Wadsworth-Emmons olefination / 7.2: Horner-Wadsworth-Emmons olefination / 10.1: Parikh-Doering oxidation / 11.1: Pinnick oxidation;

DOI:10.1002/anie.201101741

Reference yield:

(2R,5S)-2-(benzyloxy)-7-methyloct-7-ene-1,5-diol (1335028-91-5) → (2R)-3-((2S,5R,6R,8S)-5-(benzyloxy)-8-((R,E)-4-((2R,4a'R,5R,6'S,8'R,8a'R)-8'-(benzyloxy)-6'-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-7'-methyleneoctahydro-3H,3'H-spiro[furan-2,2'-pyrano[3,2-b]pyran]-5-yl)but-3-en-2-yl)-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-hydroxy-2-methylpropanoic acid (1335029-06-5)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 12 h

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 - -40 °C

2.2: 12 h / -40 - 25 °C

3.1: 1H-imidazole; dmap / dichloromethane / 3 h

4.1: AD-mix-β; water / tert-butyl alcohol / 24 h / 0 °C

5.1: pyridinium p-toluenesulfonate / dichloromethane / 2.5 h

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h

7.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium hydrogencarbonate / dichloromethane / 12 h

8.1: n-butyllithium / tetrahydrofuran; hexane / 0.67 h / -78 °C

8.2: 1 h / -78 °C

8.3: -78 - 20 °C

9.1: dmap; triethylamine / dichloromethane / 0.83 h / 0 °C

10.1: copper(l) iodide / diethyl ether / -78 - -30 °C / Inert atmosphere

10.2: 1 h / -78 °C / Inert atmosphere

10.3: -78 - 20 °C

11.1: pyridinium p-toluenesulfonate / methanol; dichloromethane / 2 h / 25 °C

12.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; tert-butyl alcohol / 0.08 h / pH 7 / aq. phosphate buffer; Sonication

13.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h

14.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 0.17 h

14.2: 20.17 h

15.1: borane-THF; ethane / tetrahydrofuran; toluene / 0.12 h / 0 °C / Inert atmosphere

15.2: 0 - 20 °C / Inert atmosphere

16.1: water; acetic acid / tetrahydrofuran / 40 h / 55 °C

17.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h

18.1: sodium chlorite; sodium dihydrogenphosphate dihydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 1 h / 0 °C

With 1H-imidazole; dmap; sodium chlorite; copper(l) iodide; n-butyllithium; sodium dihydrogenphosphate dihydrate; borane-THF; 2-methyl-but-2-ene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ethane; [bis(acetoxy)iodo]benzene; AD-mix-β; tetrabutyl ammonium fluoride; water; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile; tert-butyl alcohol; 4.1: Sharpless dihydroxylation / 14.1: Horner-Wadsworth-Emmons olefination / 14.2: Horner-Wadsworth-Emmons olefination / 17.1: Parikh-Doering oxidation / 18.1: Pinnick oxidation;

DOI:10.1002/anie.201101741

upstream raw materials:

(S)-2-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)propan-1-ol

(2R,5S)-2-(benzyloxy)-7-methyloct-7-ene-1,5-diol

(3R,6S)-3-(benzyloxy)-6-(2-methylallyl)tetrahydro-2H-pyran-2-one

(((2R,3R,6S)-3-(benzyloxy)-6-(2-methylallyl)tetrahydro-2H-pyran-2-yl)oxy)(tert-butyl)dimethylsilane