(2S,12S)-(-)-2,12-bis(tetrahydropyranyloxy)-7-trityl-7-aza-4,10-dioxatridecane

Base Information

• Chemical Name: (2S,12S)-(-)-2,12-bis(tetrahydropyranyloxy)-7-trityl-7-aza-4,10-dioxatridecane
• CAS No.: 143331-41-3
• Molecular Formula: C₃₉H₅₃NO₆
• Molecular Weight: 631.853
• Mol file: 143331-41-3.mol

Synonyms:

Chemical Property of (2S,12S)-(-)-2,12-bis(tetrahydropyranyloxy)-7-trityl-7-aza-4,10-dioxatridecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,12S)-(-)-2,12-bis(tetrahydropyranyloxy)-7-trityl-7-aza-4,10-dioxatridecane

There total 4 articles about (2S,12S)-(-)-2,12-bis(tetrahydropyranyloxy)-7-trityl-7-aza-4,10-dioxatridecane 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:

3,4-dihydro-2H-pyran (110-87-2) → (2S,12S)-(-)-2,12-bis(tetrahydropyranyloxy)-7-trityl-7-aza-4,10-dioxatridecane (143331-41-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / pyridinium tosylate / CH₂Cl₂ / 1) 0 deg C, 3 h, 2) room temperature, 20 h

2: 92 percent / LiAlH₄ / diethyl ether / 1) 0 deg C, 1 h, 2) room temperature, 1 h, 3) reflux, 20 h

3: 97 percent / KOH / tetrahydrofuran / 1) 0 deg C, 3 h, 2) room temperature, 24 h

4: 1) NaH / 1) DMF, mineral oil, a) 0 deg C, 10 min, b) room temperature, 10 min, c) 70 deg C, 90 min, 2a) 0 deg C, 10 min, b) room temperature, 10 min, c) 70 deg C, 86 h

With potassium hydroxide; lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; sodium hydride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo00046a020

Reference yield:

Ethyl (S)-(-)-2-tetrahydropyran-2-yloxypropionate (3539-40-0,73208-70-5,83780-59-0,92077-90-2,92077-91-3) → (2S,12S)-(-)-2,12-bis(tetrahydropyranyloxy)-7-trityl-7-aza-4,10-dioxatridecane (143331-41-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / LiAlH₄ / diethyl ether / 1) 0 deg C, 1 h, 2) room temperature, 1 h, 3) reflux, 20 h

2: 97 percent / KOH / tetrahydrofuran / 1) 0 deg C, 3 h, 2) room temperature, 24 h

3: 1) NaH / 1) DMF, mineral oil, a) 0 deg C, 10 min, b) room temperature, 10 min, c) 70 deg C, 90 min, 2a) 0 deg C, 10 min, b) room temperature, 10 min, c) 70 deg C, 86 h

With potassium hydroxide; lithium aluminium tetrahydride; sodium hydride; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jo00046a020

Reference yield:

(S)-(-)-2-(tetrahydropyranyloxy)propanol (3539-39-7,76946-21-9,83780-60-3,92077-92-4,92077-93-5,124508-75-4,124508-76-5) → (2S,12S)-(-)-2,12-bis(tetrahydropyranyloxy)-7-trityl-7-aza-4,10-dioxatridecane (143331-41-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / KOH / tetrahydrofuran / 1) 0 deg C, 3 h, 2) room temperature, 24 h

2: 1) NaH / 1) DMF, mineral oil, a) 0 deg C, 10 min, b) room temperature, 10 min, c) 70 deg C, 90 min, 2a) 0 deg C, 10 min, b) room temperature, 10 min, c) 70 deg C, 86 h

With potassium hydroxide; sodium hydride; In tetrahydrofuran;

DOI:10.1021/jo00046a020

upstream raw materials:

N,N-[bis(2-hydroxyethyl)]-N-(triphenylmethyl)amine

(S)-(-)-2-(tetrahydropyranyloxy)propyl p-toluenesulfonate

3,4-dihydro-2H-pyran

Ethyl (S)-(-)-2-tetrahydropyran-2-yloxypropionate