<1S,2S-3(E)>-(<1-(<2-(benzyloxy)-1(S)-methyl>ethyl)-2-hydroxy-3-pentenyl>-oxy)acetic acid 1,1-dimethylethyl ester

Base Information

• Chemical Name: <1S,2S-3(E)>-(<1-(<2-(benzyloxy)-1(S)-methyl>ethyl)-2-hydroxy-3-pentenyl>-oxy)acetic acid 1,1-dimethylethyl ester
• CAS No.: 96720-58-0
• Molecular Formula: C₂₁H₃₂O₅
• Molecular Weight: 364.482
• Mol file: 96720-58-0.mol

Synonyms:<1S,2S-3(E)>-(<1-(<2-(benzyloxy)-1(S)-methyl>ethyl)-2-hydroxy-3-pentenyl>-oxy)acetic acid 1,1-dimethylethyl ester

Chemical Property of <1S,2S-3(E)>-(<1-(<2-(benzyloxy)-1(S)-methyl>ethyl)-2-hydroxy-3-pentenyl>-oxy)acetic acid 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <1S,2S-3(E)>-(<1-(<2-(benzyloxy)-1(S)-methyl>ethyl)-2-hydroxy-3-pentenyl>-oxy)acetic acid 1,1-dimethylethyl ester

There total 5 articles about <1S,2S-3(E)>-(<1-(<2-(benzyloxy)-1(S)-methyl>ethyl)-2-hydroxy-3-pentenyl>-oxy)acetic acid 1,1-dimethylethyl ester 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:

(E)-propenyl lithium (6386-72-7,6524-17-0,29283-76-9) + (1S,2S)-<3-(benzyloxy)-1-formyl-2-methylpropoxy>acetic acid 1,1-dimethylethyl ester (96720-57-9) → <1S,2R-3(E)>-(<1-(<2-(benzyloxy)-1(S)-methyl>ethyl)-2-hydroxy-3-pentenyl>-oxy)acetic acid 1,1-dimethylethyl ester (96789-96-7) + <1S,2S-3(E)>-(<1-(<2-(benzyloxy)-1(S)-methyl>ethyl)-2-hydroxy-3-pentenyl>-oxy)acetic acid 1,1-dimethylethyl ester (96720-58-0)

Guidance literature:

With CuI*P(n-Bu)3; In diethyl ether; at -78 ℃; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)98423-5

Reference yield:

(3R,4S)-5-(benzyloxy)-3-hydroxy-4-methyl-1-pentene (96720-54-6) → <1S,2S-3(E)>-(<1-(<2-(benzyloxy)-1(S)-methyl>ethyl)-2-hydroxy-3-pentenyl>-oxy)acetic acid 1,1-dimethylethyl ester (96720-58-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / NaH / tetrahydrofuran / 12 h / Heating

2: 88 percent / DMAP, DCC / CH₂Cl₂ / 3 h / 25 °C

3: 1.) O₃; 2.) Me₂S / 1.) methylene dichloride, -78 deg C; 2.) room temp., 2 h

4: diethyl ether / 2 h / -78 °C

With dmap; dimethylsulfide; sodium hydride; ozone; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4020(01)90568-X

Reference yield:

(1R,2S)-<3-(benzyloxy)-2-methyl-1-(ethenyl)propoxy>acetic acid (96720-55-7) → <1S,2S-3(E)>-(<1-(<2-(benzyloxy)-1(S)-methyl>ethyl)-2-hydroxy-3-pentenyl>-oxy)acetic acid 1,1-dimethylethyl ester (96720-58-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / DMAP, DCC / CH₂Cl₂ / 3 h / 25 °C

2: 1.) O₃; 2.) Me₂S / 1.) methylene dichloride, -78 deg C; 2.) room temp., 2 h

3: diethyl ether / 2 h / -78 °C

With dmap; dimethylsulfide; ozone; dicyclohexyl-carbodiimide; In diethyl ether; dichloromethane;

DOI:10.1016/S0040-4020(01)90568-X

upstream raw materials:

(E)-propenyl lithium

(1S,2S)-<3-(benzyloxy)-1-formyl-2-methylpropoxy>acetic acid 1,1-dimethylethyl ester

(2S)-3-(benzyloxy)-2-methylpropanal

(3R,4S)-5-(benzyloxy)-3-hydroxy-4-methyl-1-pentene

Downstream raw materials:

<1S-3(E)>-(<1-(<2-(benzyloxy)-1(S)-methyl>ethyl)-2-oxo-3-pentenyl>oxy)acetic acid 1,1-dimethylethyl ester

(5S,6S)-5-<2-(benzyloxy)-1(S)-methyl>ethyl-6-<1(E)-propenyl>-1,4-dioxan-2-one

(2R,3S,6R-)-6-<2-(benzyloxy)-1(S)-methyl>ethyl-3,6-dihydro-2-(1-hydroxypropyl)-3-methyl-2H-pyran

(5S,6R)-5-<2-(benzyloxy)-1(S)-methyl>ethyl-6-<1(E)-propenyl>-1,4-dioxan-2-one