dimethyl (4-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-2-oxobutyl)phosphonate

Base Information

• Chemical Name: dimethyl (4-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-2-oxobutyl)phosphonate
• CAS No.: 1335028-86-8
• Molecular Formula: C₄₄H₆₃O₁₁P
• Molecular Weight: 798.951

Synonyms:

Chemical Property of dimethyl (4-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-2-oxobutyl)phosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl (4-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-2-oxobutyl)phosphonate

There total 17 articles about dimethyl (4-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-2-oxobutyl)phosphonate 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:

C44H65O11P → dimethyl (4-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-2-oxobutyl)phosphonate (1335028-86-8)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.75h;

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) → dimethyl (4-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-2-oxobutyl)phosphonate (1335028-86-8)

Guidance literature:

Multi-step reaction with 6 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

With pyridine; sodium periodate; osmium(VIII) oxide; carbon tetrabromide; tert.-butyl lithium; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; In tetrahydrofuran; diethyl ether; dichloromethane; water; mineral oil; pentane;

DOI:10.1002/anie.201101741

Reference yield:

C25H31NO5 → dimethyl (4-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)-2-oxobutyl)phosphonate (1335028-86-8)

Guidance literature:

Multi-step reaction with 12 steps

1.1: sodium tetrahydroborate; water / tetrahydrofuran / 14 h / 0 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 - 20 °C

2.2: 72 h / 0 - 20 °C

3.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; tert-butyl alcohol / 2 h / 25 °C / pH 7 / aq. buffer

4.1: sulfur trioxide pyridine complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C

5.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 0.25 h / 25 °C

5.2: 16 h / 25 °C

6.1: 20 % Pd(OH)2/C; hydrogen / ethanol / 15 h / 760.05 Torr

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

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

8.2: 0.5 h / -78 °C

8.3: -78 - 25 °C

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

9.2: 16 h / 0 - 20 °C

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

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

11.2: 0.75 h / -78 °C / Inert atmosphere

11.3: -78 - 20 °C / Inert atmosphere

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

With pyridine; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; carbon tetrabromide; 20 % Pd(OH)2/C; water; hydrogen; tert.-butyl lithium; sulfur trioxide pyridine complex; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; acetonitrile; mineral oil; tert-butyl alcohol; pentane; 4.1: Parikh-Doering oxidation / 5.1: Horner-Wadsworth-Emmons olefination / 5.2: 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

C₁₄H₂₂O₄

(3S,4S)-3,5-bis(benzyloxy)-4-methylpentan-1-ol

(3S,4S)-3,5-bis(benzyloxy)-4-methylpentanal

Downstream raw materials:

(6R,E)-6-((2S,6R,8S,11R)-11-(benzyloxy)-4-methyl-8-(((R)-2,2,4-trimethyl-1,3-dioxolan-4-yl)methyl)-1,7-dioxaspiro[5.5]undec-4-en-2-yl)-1-((2S,4aR,6S,8R,8aR)-8-(benzyloxy)-6-((1S,3S)-1-(benzyloxy)-3-((2S,6R,11S)-11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)butyl)-2-methoxy-7-methyleneoctahydropyrano[3,2-b]pyran-2-yl)hept-4-en-3-one

(2S)-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

(2S)-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

(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

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