{4-Benzyloxy-1-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-but-2-ynyloxymethyl}-carbamic acid cyclohexyl ester

Base Information

• Chemical Name: {4-Benzyloxy-1-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-but-2-ynyloxymethyl}-carbamic acid cyclohexyl ester
• CAS No.: 118972-84-2
• Molecular Formula: C₂₉H₃₂N₂O₆
• Molecular Weight: 504.583
• Mol file: 118972-84-2.mol

Synonyms:{4-Benzyloxy-1-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-but-2-ynyloxymethyl}-carbamic acid cyclohexyl ester

Chemical Property of {4-Benzyloxy-1-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-but-2-ynyloxymethyl}-carbamic acid cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {4-Benzyloxy-1-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-but-2-ynyloxymethyl}-carbamic acid cyclohexyl ester

There total 4 articles about {4-Benzyloxy-1-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-but-2-ynyloxymethyl}-carbamic acid cyclohexyl 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: 69.0%

cyclohexyl (N-hydroxymethyl)carbamate (60794-21-0) + 2-(6-Benzyloxy-3-hydroxy-hex-4-ynyl)-isoindole-1,3-dione (118972-83-1) → {4-Benzyloxy-1-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-but-2-ynyloxymethyl}-carbamic acid cyclohexyl ester (118972-84-2)

Guidance literature:

With toluene-4-sulfonic acid; In diethyl ether;

DOI:10.1016/S0040-4039(00)82116-4

Reference yield:

N-(3-butenyl)phthalimide (52898-32-5) → {4-Benzyloxy-1-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-but-2-ynyloxymethyl}-carbamic acid cyclohexyl ester (118972-84-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) O₃; 2) dimethyl sulfide, sodium acetate / 1) MeOH, CH₂Cl₂, -78 deg C;

2: 56 percent / tetrahydrofuran / -78 °C

3: 69 percent / TsOH / diethyl ether

With dimethylsulfide; sodium acetate; toluene-4-sulfonic acid; ozone; In tetrahydrofuran; diethyl ether;

DOI:10.1016/S0040-4039(00)82116-4

Reference yield:

3-(N-phthaloyl)propionaldehyde (2436-29-5) → {4-Benzyloxy-1-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-but-2-ynyloxymethyl}-carbamic acid cyclohexyl ester (118972-84-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 56 percent / tetrahydrofuran / -78 °C

2: 69 percent / TsOH / diethyl ether

With toluene-4-sulfonic acid; In tetrahydrofuran; diethyl ether;

DOI:10.1016/S0040-4039(00)82116-4

upstream raw materials:

cyclohexyl (N-hydroxymethyl)carbamate

2-(6-Benzyloxy-3-hydroxy-hex-4-ynyl)-isoindole-1,3-dione

N-(3-butenyl)phthalimide

3-(N-phthaloyl)propionaldehyde

Downstream raw materials:

{(Z)-4-Benzyloxy-1-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-but-2-enyloxymethyl}-carbamic acid cyclohexyl ester

4-Benzyloxymethyl-6-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-[1,3]oxazinane-3-carboxylic acid cyclohexyl ester

(4S,5S)-4-(2-Benzyloxy-ethyl)-5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-oxazolidine-3-carboxylic acid cyclohexyl ester

(4S,5S)-4-Carboxymethyl-5-[2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-oxazolidine-3-carboxylic acid cyclohexyl ester