(3R,7S,10R,Z)-2-[(2S,6R)-6-allyl-tetrahydro-2H-pyran-2-yl]-10-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-7-(4-methoxybenzyloxy)-2-methyldodec-8-en-5-one

Base Information

Chemical Name:(3R,7S,10R,Z)-2-[(2S,6R)-6-allyl-tetrahydro-2H-pyran-2-yl]-10-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-7-(4-methoxybenzyloxy)-2-methyldodec-8-en-5-one
CAS No.:1433460-08-2
Molecular Formula:C₄₆H₆₄O₆Si
Molecular Weight:741.096
Hs Code.:

(3R,7S,10R,Z)-2-[(2S,6R)-6-allyl-tetrahydro-2H-pyran-2-yl]-10-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-7-(4-methoxybenzyloxy)-2-methyldodec-8-en-5-one

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Chemical Property of (3R,7S,10R,Z)-2-[(2S,6R)-6-allyl-tetrahydro-2H-pyran-2-yl]-10-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-7-(4-methoxybenzyloxy)-2-methyldodec-8-en-5-one

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Technology Process of (3R,7S,10R,Z)-2-[(2S,6R)-6-allyl-tetrahydro-2H-pyran-2-yl]-10-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-7-(4-methoxybenzyloxy)-2-methyldodec-8-en-5-one

There total 15 articles about (3R,7S,10R,Z)-2-[(2S,6R)-6-allyl-tetrahydro-2H-pyran-2-yl]-10-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-7-(4-methoxybenzyloxy)-2-methyldodec-8-en-5-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:

: 1433460-01-5
(4S,7R,Z)-7-[(tert-butyldiphenylsilyloxy)methyl]-4-(4-methoxybenzyloxy)non-5-en-2-one

: 1433460-05-9
2-[(2S,6R)-6-allyl-tetrahydro-2H-pyran-2-yl]-2-methylpropanal

: 1433460-07-1
(3S,7S,10R,Z)-2-[(2S,6R)-6-allyl-tetrahydro-2H-pyran-2-yl]-10-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-7-(4-methoxybenzyloxy)-2-methyldodec-8-en-5-one

: 1433460-08-2
(3R,7S,10R,Z)-2-[(2S,6R)-6-allyl-tetrahydro-2H-pyran-2-yl]-10-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-7-(4-methoxybenzyloxy)-2-methyldodec-8-en-5-one

Guidance literature:: (4S,7R,Z)-7-[(tert-butyldiphenylsilyloxy)methyl]-4-(4-methoxybenzyloxy)non-5-en-2-one; With dicyclohexylboron chloride; triethylamine; In diethyl ether; hexane; dichloromethane; at 0 ℃; for 1.5h; Inert atmosphere;

2-[(2S,6R)-6-allyl-tetrahydro-2H-pyran-2-yl]-2-methylpropanal; In diethyl ether; hexane; dichloromethane; at -85 - -78 ℃; for 3.5h; Overall yield = 83 %; Overall yield = 160 mg;
DOI:10.1002/ejoc.201201728

Reference yield:

: 947619-70-7
(S)-2-(4-methoxybenzyloxy)pent-4-enal

: 1433460-07-1
(3S,7S,10R,Z)-2-[(2S,6R)-6-allyl-tetrahydro-2H-pyran-2-yl]-10-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-7-(4-methoxybenzyloxy)-2-methyldodec-8-en-5-one

: 1433460-08-2
(3R,7S,10R,Z)-2-[(2S,6R)-6-allyl-tetrahydro-2H-pyran-2-yl]-10-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-7-(4-methoxybenzyloxy)-2-methyldodec-8-en-5-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

1.2: -80 - 20 °C

2.1: copper(l) chloride; palladium dichloride; oxygen / N,N-dimethyl-formamide; water; diethyl ether / 120 h / 20 °C

2.2: 16 h / 20 °C

3.1: triethylamine; dicyclohexylboron chloride / dichloromethane; diethyl ether; hexane / 1.5 h / 0 °C / Inert atmosphere

3.2: 3.5 h / -85 - -78 °C

With dicyclohexylboron chloride; oxygen; potassium hexamethylsilazane; triethylamine; copper(l) chloride; palladium dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; 1.2: |Wittig Olefination;
DOI:10.1002/ejoc.201201728

Reference yield:

: 2612-29-5
2-ethyl-1,3-propandiol

: 1433460-07-1
(3S,7S,10R,Z)-2-[(2S,6R)-6-allyl-tetrahydro-2H-pyran-2-yl]-10-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-7-(4-methoxybenzyloxy)-2-methyldodec-8-en-5-one

: 1433460-08-2
(3R,7S,10R,Z)-2-[(2S,6R)-6-allyl-tetrahydro-2H-pyran-2-yl]-10-[(tert-butyldiphenylsilyloxy)methyl]-3-hydroxy-7-(4-methoxybenzyloxy)-2-methyldodec-8-en-5-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran / 1 h / -25 °C / Inert atmosphere

1.2: -30 °C

2.1: triphenylphosphine; N-iodo-succinimide / dichloromethane / 13 h / 0 - 20 °C / Inert atmosphere

3.1: toluene / 90 h / Reflux

4.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

4.2: -80 - 20 °C

5.1: copper(l) chloride; palladium dichloride; oxygen / N,N-dimethyl-formamide; water; diethyl ether / 120 h / 20 °C

5.2: 16 h / 20 °C

6.1: triethylamine; dicyclohexylboron chloride / dichloromethane; diethyl ether; hexane / 1.5 h / 0 °C / Inert atmosphere

6.2: 3.5 h / -85 - -78 °C

With N-iodo-succinimide; n-butyllithium; dicyclohexylboron chloride; oxygen; potassium hexamethylsilazane; triethylamine; triphenylphosphine; copper(l) chloride; palladium dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 4.2: |Wittig Olefination;
DOI:10.1002/ejoc.201201728