(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl N,N-diisopropyl phosphoramidite

Base Information

• Chemical Name: (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl N,N-diisopropyl phosphoramidite
• CAS No.: 637004-85-4
• Molecular Formula: C₂₇H₄₀NO₁₁P
• Molecular Weight: 585.588
• Mol file: 637004-85-4.mol

Synonyms:(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl N,N-diisopropyl phosphoramidite

Chemical Property of (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl N,N-diisopropyl phosphoramidite

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl N,N-diisopropyl phosphoramidite

There total 4 articles about (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl N,N-diisopropyl phosphoramidite 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: 79.0%

(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl) bis-N,N-diisopropyl phosphoramidite (849063-81-6) + benzyl alcohol (100-51-6,185532-71-2) → (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl N,N-diisopropyl phosphoramidite (637004-85-4)

Guidance literature:

With 1H-tetrazole; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/jo048443z

Reference yield: 59.0%

2,3,4,6-tetra-O-acetyl-D-mannopyranose (3947-62-4,6207-76-7,10343-06-3,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1) + (benzyloxy)chloro(diisopropylamino)phosphane (128753-68-4) → (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl N,N-diisopropyl phosphoramidite (637004-85-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1055/s-2003-40344

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose (22860-22-6) → (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl N,N-diisopropyl phosphoramidite (637004-85-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / diisopropyl(ethyl)amine / CH₂Cl₂ / 6 h / 20 °C

2: 79 percent / 1H-tetrazole / CH₂Cl₂ / 4 h / 20 °C

With 1H-tetrazole; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/jo048443z

upstream raw materials:

2,3,4,6-tetra-O-acetyl-D-mannopyranose

(benzyloxy)chloro(diisopropylamino)phosphane

(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl) bis-N,N-diisopropyl phosphoramidite

benzyl alcohol

Downstream raw materials:

benzyl {{[(S)-2-allyloxycarbonyl-2-(9-fluorenylmethoxycarbonylamino)]ethyl}-2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl}phosphate

benzyl {{[(S)-2-hydroxycarbonyl-2-(9-fluorenylmethoxycarbonylamino)]ethyl}-2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl}phosphate

Acetic acid (2R,3R,4S,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-{[(S)-2-[(S)-2-((S)-2-acetylamino-3-benzyloxy-propionylamino)-3-benzyloxy-propionylamino]-2-((S)-1-carbamoyl-ethylcarbamoyl)-ethoxy]-hydroxy-phosphoryloxy}-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{[(S)-2-[(S)-2-((S)-2-acetylamino-3-benzyloxy-propionylamino)-3-benzyloxy-propionylamino]-2-((S)-1-carbamoyl-ethylcarbamoyl)-ethoxy]-benzyloxy-phosphoryloxy}-tetrahydro-pyran-3-yl ester