(2R,3S,5R,9S)-3-benzyloxy-1,2-(isopropylidenedioxy)-9-methyl-11-(p-toluenesulfonyloxy)-5-(p-toluenesulfonyloxymethyl)undecane

Base Information

Chemical Name:(2R,3S,5R,9S)-3-benzyloxy-1,2-(isopropylidenedioxy)-9-methyl-11-(p-toluenesulfonyloxy)-5-(p-toluenesulfonyloxymethyl)undecane
CAS No.:913647-55-9
Molecular Formula:C₃₇H₅₀O₉S₂
Molecular Weight:702.931
Hs Code.:

Synonyms:(2R,3S,5R,9S)-3-benzyloxy-1,2-(isopropylidenedioxy)-9-methyl-11-(p-toluenesulfonyloxy)-5-(p-toluenesulfonyloxymethyl)undecane

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Chemical Property of (2R,3S,5R,9S)-3-benzyloxy-1,2-(isopropylidenedioxy)-9-methyl-11-(p-toluenesulfonyloxy)-5-(p-toluenesulfonyloxymethyl)undecane

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Technology Process of (2R,3S,5R,9S)-3-benzyloxy-1,2-(isopropylidenedioxy)-9-methyl-11-(p-toluenesulfonyloxy)-5-(p-toluenesulfonyloxymethyl)undecane

There total 6 articles about (2R,3S,5R,9S)-3-benzyloxy-1,2-(isopropylidenedioxy)-9-methyl-11-(p-toluenesulfonyloxy)-5-(p-toluenesulfonyloxymethyl)undecane 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: 91.0%

: 913647-54-8
(2R,6S)-2-[(2S,3R)-2-benzyloxy-3,4-(isopropylidenedioxy)butyl]-6-methyloctane-1,8-diol

: 98-59-9
p-toluenesulfonyl chloride

: 913647-55-9
(2R,3S,5R,9S)-3-benzyloxy-1,2-(isopropylidenedioxy)-9-methyl-11-(p-toluenesulfonyloxy)-5-(p-toluenesulfonyloxymethyl)undecane

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃;
DOI:10.1016/j.tet.2006.07.054

Reference yield:

: ethyl (R)-5-iodo-3-methylpentanoate

: 913647-55-9
(2R,3S,5R,9S)-3-benzyloxy-1,2-(isopropylidenedioxy)-9-methyl-11-(p-toluenesulfonyloxy)-5-(p-toluenesulfonyloxymethyl)undecane

Guidance literature:: Multi-step reaction with 3 steps

1.1: MgBr₂*OEt₂ / CH₂Cl₂ / 0.25 h / 20 °C

1.2: n-Bu₃SnH; Et₃B / hexane / 6 h / 0 °C

1.3: 71 percent / KF / hexane; H₂O / 20 °C

2.1: 89 percent / lithium aluminium hydride / diethyl ether / 12 h / 20 °C

3.1: 91 percent / pyridine / CH₂Cl₂ / 20 °C

With pyridine; lithium aluminium tetrahydride; magnesium bromide; In diethyl ether; dichloromethane;
DOI:10.1016/j.tet.2006.07.054

Reference yield:

: 913647-47-9
ethyl (4S,5R)-4-benzyloxy-5,6-(isopropylidenedioxy)-2-methylenehexanoate

: 913647-55-9
(2R,3S,5R,9S)-3-benzyloxy-1,2-(isopropylidenedioxy)-9-methyl-11-(p-toluenesulfonyloxy)-5-(p-toluenesulfonyloxymethyl)undecane

Guidance literature:: Multi-step reaction with 3 steps

1.1: MgBr₂*OEt₂ / CH₂Cl₂ / 0.25 h / 20 °C

1.2: n-Bu₃SnH; Et₃B / hexane / 6 h / 0 °C

1.3: 71 percent / KF / hexane; H₂O / 20 °C

2.1: 89 percent / lithium aluminium hydride / diethyl ether / 12 h / 20 °C

3.1: 91 percent / pyridine / CH₂Cl₂ / 20 °C

With pyridine; lithium aluminium tetrahydride; magnesium bromide; In diethyl ether; dichloromethane;
DOI:10.1016/j.tet.2006.07.054