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

Base Information

• Chemical Name: benzyl {{[(S)-2-allyloxycarbonyl-2-(9-fluorenylmethoxycarbonylamino)]ethyl}-2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl}phosphate
• CAS No.: 637004-86-5
• Molecular Formula: C₄₂H₄₆NO₁₇P
• Molecular Weight: 867.798
• Mol file: 637004-86-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about benzyl {{[(S)-2-allyloxycarbonyl-2-(9-fluorenylmethoxycarbonylamino)]ethyl}-2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl}phosphate 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: 73.0%

N-(9-fluorenylmethoxycarbonyl)-L-serine allyl ester (136497-85-3) + (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl N,N-diisopropyl phosphoramidite (637004-85-4) → benzyl {{[(S)-2-allyloxycarbonyl-2-(9-fluorenylmethoxycarbonylamino)]ethyl}-2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl}phosphate (637004-86-5)

Guidance literature:

N-(9-fluorenylmethoxycarbonyl)-L-serine allyl ester; (2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)benzyl N,N-diisopropyl phosphoramidite; With 1H-tetrazole; In acetonitrile; at 20 ℃; for 4h;

With tert.-butylhydroperoxide; In decane; acetonitrile; at -40 ℃; for 3h;

DOI:10.1021/jo048443z

Reference yield:

(S)-3-[Benzyloxy-((2R,3S,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-phosphanyloxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid allyl ester → benzyl {{[(S)-2-allyloxycarbonyl-2-(9-fluorenylmethoxycarbonylamino)]ethyl}-2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl}phosphate (637004-86-5)

Guidance literature:

With tert.-butylhydroperoxide; In decane; acetonitrile; at -40 ℃;

DOI:10.1055/s-2003-40344

Reference yield:

(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl) bis-N,N-diisopropyl phosphoramidite (849063-81-6) → benzyl {{[(S)-2-allyloxycarbonyl-2-(9-fluorenylmethoxycarbonylamino)]ethyl}-2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl}phosphate (637004-86-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 79 percent / 1H-tetrazole / CH₂Cl₂ / 4 h / 20 °C

2.1: 1H-tetrazole / acetonitrile / 4 h / 20 °C

2.2: 73 percent / tBuOOH / decane; acetonitrile / 3 h / -40 °C

With 1H-tetrazole; In dichloromethane; acetonitrile;

DOI:10.1021/jo048443z

upstream raw materials:

N-(9-fluorenylmethoxycarbonyl)-L-serine allyl ester

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

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

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

Downstream raw materials:

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