O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serine tert-Butyl Ester

Base Information

• Chemical Name: O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serine tert-Butyl Ester
• CAS No.: 878483-02-4
• Molecular Formula: C35H38 N4 O9
• Molecular Weight: 658.7
• DSSTox Substance ID: DTXSID80693676
• Mol file: 878483-02-4.mol

Synonyms:O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serine tert-Butyl Ester;878483-02-4;tert-butyl (2S)-3-[[(4aS,6S,7S,8R,8aR)-7-azido-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoate;O-(2-Azido-4,6-O-benzylidene-2-deoxy-|A-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serine tert-Butyl Ester;DTXSID80693676;MFCD11112166;Fmoc-Ser[GalN3[46Bzd]-alpha]-OtBu;HY-W142082;CS-0201866;D88470;tert-Butyl (2S)-3-{[(4aS,6S,7S,8R,8aR)-7-azido-8-hydroxy-2-phenylhexahydro-2H-pyrano[3,2-d][1,3]dioxin-6-yl]oxy}-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoate (non-preferred name)

Chemical Property of O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serine tert-Butyl Ester

Chemical Property:

• PSA: 175.02000
• LogP: 4.78806
• Storage Temp.: <0°C
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 12
• Exact Mass: 658.26387880
• Heavy Atom Count: 48
• Complexity: 1130

Purity/Quality:

98%,99%, ^*data from raw suppliers

O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serine tert-Butyl Ester >92.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)C(COC1C(C(C2C(O1)COC(O2)C3=CC=CC=C3)O)N=[N+]=[N-])NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46
• Isomeric SMILES: CC(C)(C)OC(=O)[C@H](CO[C@@H]1[C@H]([C@H]([C@@H]2[C@@H](O1)COC(O2)C3=CC=CC=C3)O)N=[N+]=[N-])NC(=O)OCC4C5=CC=CC=C5C6=CC=CC=C46

Technology Process of O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serine tert-Butyl Ester

There total 2 articles about O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serine tert-Butyl 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:

benzaldehyde dimethyl acetal (1125-88-8) + C28H34N4O9 (1257307-76-8) → N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-(2-azido-2-deoxy-4,6-O-benzylidene-α-D-galactopyranosyl)-L-serine tert-butyl ester (878483-02-4)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1021/ol402845e

Reference yield:

N-(9-Fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-desoxy-α-D-galactopyranosyl)-L-serin-tert-butylester (110797-36-9) → N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-(2-azido-2-deoxy-4,6-O-benzylidene-α-D-galactopyranosyl)-L-serine tert-butyl ester (878483-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methylate / methanol / 5 h / 20 °C / pH 8 - 8.5

2: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 18 h / 20 °C

With sodium methylate; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/ol402845e

Reference yield: 73.0%

N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-(2-azido-2-deoxy-4,6-O-benzylidene-α-D-galactopyranosyl)-L-serine tert-butyl ester (878483-02-4) + 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate (86520-63-0) → N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-[O-(2'',3'',4''-6''-tetra-O-acetyl-β-D-galactopyranosyl)-(1''-3)-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)]-L-serine tert-butyl ester (1477460-73-3)

Guidance literature:

N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-(2-azido-2-deoxy-4,6-O-benzylidene-α-D-galactopyranosyl)-L-serine tert-butyl ester; 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate; In 1,2-dichloro-ethane; at 20 ℃; for 0.5h; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at -20 ℃; for 1h; Molecular sieve;

DOI:10.1021/ol402845e

upstream raw materials:

N-(9-Fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-azido-2-desoxy-α-D-galactopyranosyl)-L-serin-tert-butylester

benzaldehyde dimethyl acetal

C₂₈H₃₄N₄O₉

Downstream raw materials:

N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-[O-(2'',3'',4''-6''-tetra-O-acetyl-β-D-galactopyranosyl)-(1''-3)-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)]-L-serine tert-butyl ester

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