(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-methylpropane-1,2-diol

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-methylpropane-1,2-diol
• CAS No.: 1335029-05-4
• Molecular Formula: C₆₅H₈₈O₁₂
• Molecular Weight: 1061.41
• Mol file: 1335029-05-4.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-methylpropane-1,2-diol

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-methylpropane-1,2-diol

There total 38 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-methylpropane-1,2-diol 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:

C69H96O13 → (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-methylpropane-1,2-diol (1335029-05-4)

Guidance literature:

With water; acetic acid; In tetrahydrofuran; at 55 ℃; for 40h;

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-methylpropane-1,2-diol (1335029-05-4)

Guidance literature:

Multi-step reaction with 9 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

With pyridine; sodium periodate; osmium(VIII) oxide; borane-THF; ethane; carbon tetrabromide; water; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; acetonitrile; mineral oil; pentane; 7.1: Horner-Wadsworth-Emmons olefination / 7.2: Horner-Wadsworth-Emmons olefination;

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-methylpropane-1,2-diol (1335029-05-4)

Guidance literature:

Multi-step reaction with 16 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

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

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

Downstream raw materials:

(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