1L-(1,2,3,4,5/0)-1,2,3-tri-O-acetyl-5-acetamido-4-O-methyl-1,2,3,4-cyclopentanetetrol

Base Information

• Chemical Name: 1L-(1,2,3,4,5/0)-1,2,3-tri-O-acetyl-5-acetamido-4-O-methyl-1,2,3,4-cyclopentanetetrol
• CAS No.: 288088-79-9
• Molecular Formula: C₁₄H₂₁NO₈
• Molecular Weight: 331.323
• Mol file: 288088-79-9.mol

Synonyms:

Chemical Property of 1L-(1,2,3,4,5/0)-1,2,3-tri-O-acetyl-5-acetamido-4-O-methyl-1,2,3,4-cyclopentanetetrol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1L-(1,2,3,4,5/0)-1,2,3-tri-O-acetyl-5-acetamido-4-O-methyl-1,2,3,4-cyclopentanetetrol

There total 4 articles about 1L-(1,2,3,4,5/0)-1,2,3-tri-O-acetyl-5-acetamido-4-O-methyl-1,2,3,4-cyclopentanetetrol 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: 87.0%

acetic anhydride (108-24-7) + C20H37NO5Si (288088-74-4) → 1L-(1,2,3,4,5/0)-1,2,3-tri-O-acetyl-5-acetamido-4-O-methyl-1,2,3,4-cyclopentanetetrol (288088-79-9)

Guidance literature:

C₂₀H₃₇NO₅Si;

acetic anhydride;

DOI:10.1016/S0960-894X(00)00162-1

Reference yield:

C23H29NO8 (171031-90-6) → 1L-(1,2,3,4,5/0)-1,2,3-tri-O-acetyl-5-acetamido-4-O-methyl-1,2,3,4-cyclopentanetetrol (288088-79-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

2.1: 66 mg / sodium methoxide / methanol; CH₂Cl₂ / 0.5 h / 0 °C

3.1: 97 percent / silver oxide / acetonitrile / 80 °C

4.1: H₂O; acetic acid / 9 h / 80 °C

4.2: 87 percent / pyridine / 20 °C

With 2,6-dimethylpyridine; sodium methylate; silver(l) oxide; In methanol; dichloromethane; water; acetic acid; acetonitrile; 2.1: Zemplen deacylation;

DOI:10.1002/ejoc.200500118

Reference yield:

C19H35NO5Si (288088-73-3) → 1L-(1,2,3,4,5/0)-1,2,3-tri-O-acetyl-5-acetamido-4-O-methyl-1,2,3,4-cyclopentanetetrol (288088-79-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 97 percent / silver oxide / acetonitrile / 80 °C

2.1: H₂O; acetic acid / 9 h / 80 °C

2.2: 87 percent / pyridine / 20 °C

With silver(l) oxide; In water; acetic acid; acetonitrile;

DOI:10.1002/ejoc.200500118

upstream raw materials:

acetic anhydride

C₂₀H₃₇NO₅Si

C₂₃H₂₉NO₈

C₁₉H₃₅NO₅Si

Downstream raw materials:

(1S,2R,3R,4R,5S)-5-amino-1-O-methyl-1,2,3,4-cyclopentanetetrol