diethyl (2R,6S)-2-[(2S,3R)-2-benzyloxy-3,4-(isopropylidenedioxy)butyl]-6-methyl-1,8-octanedioate

Base Information

Chemical Name:diethyl (2R,6S)-2-[(2S,3R)-2-benzyloxy-3,4-(isopropylidenedioxy)butyl]-6-methyl-1,8-octanedioate
CAS No.:913647-53-7
Molecular Formula:C₂₇H₄₂O₇
Molecular Weight:478.626
Hs Code.:

Synonyms:diethyl (2R,6S)-2-[(2S,3R)-2-benzyloxy-3,4-(isopropylidenedioxy)butyl]-6-methyl-1,8-octanedioate

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Chemical Property of diethyl (2R,6S)-2-[(2S,3R)-2-benzyloxy-3,4-(isopropylidenedioxy)butyl]-6-methyl-1,8-octanedioate

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Technology Process of diethyl (2R,6S)-2-[(2S,3R)-2-benzyloxy-3,4-(isopropylidenedioxy)butyl]-6-methyl-1,8-octanedioate

There total 4 articles about diethyl (2R,6S)-2-[(2S,3R)-2-benzyloxy-3,4-(isopropylidenedioxy)butyl]-6-methyl-1,8-octanedioate 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: 71.0%

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

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

: 913647-53-7
diethyl (2R,6S)-2-[(2S,3R)-2-benzyloxy-3,4-(isopropylidenedioxy)butyl]-6-methyl-1,8-octanedioate

Guidance literature:: ethyl (4S,5R)-4-benzyloxy-5,6-(isopropylidenedioxy)-2-methylenehexanoate; With magnesium bromide; In dichloromethane; at 20 ℃; for 0.25h;

ethyl (R)-5-iodo-3-methylpentanoate; With triethyl borane; tri-n-butyl-tin hydride; In hexane; at 0 ℃; for 6h;

With potassium fluoride; In hexane; water; at 20 ℃;
DOI:10.1016/j.tet.2006.07.054

Reference yield:

: 100-39-0
benzyl bromide

: 913647-53-7
diethyl (2R,6S)-2-[(2S,3R)-2-benzyloxy-3,4-(isopropylidenedioxy)butyl]-6-methyl-1,8-octanedioate

Guidance literature:: Multi-step reaction with 2 steps

1.1: NH₄Cl; zinc / H₂O; tetrahydrofuran / 3 h / 0 °C

1.2: 14 mg / silver(I) oxide / toluene / 48 h / 20 °C

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

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

2.3: 71 percent / KF / hexane; H₂O / 20 °C

With ammonium chloride; magnesium bromide; zinc; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.tet.2006.07.054

Reference yield:

: 15186-48-8
2,3-isopropylidene-glyceraldehyde

: 913647-53-7
diethyl (2R,6S)-2-[(2S,3R)-2-benzyloxy-3,4-(isopropylidenedioxy)butyl]-6-methyl-1,8-octanedioate

Guidance literature:: Multi-step reaction with 2 steps

1.1: NH₄Cl; zinc / H₂O; tetrahydrofuran / 3 h / 0 °C

1.2: 14 mg / silver(I) oxide / toluene / 48 h / 20 °C

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

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

2.3: 71 percent / KF / hexane; H₂O / 20 °C

With ammonium chloride; magnesium bromide; zinc; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.tet.2006.07.054