O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-Fmoc-L-threonine tert-Butyl Ester

Base Information

• Chemical Name: O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-Fmoc-L-threonine tert-Butyl Ester
• CAS No.: 195976-07-9
• Molecular Formula: C36H40 N4 O9
• Molecular Weight: 672.735
• DSSTox Substance ID: DTXSID20693675
• Mol file: 195976-07-9.mol

Synonyms:195976-07-9;O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-Fmoc-L-threonine tert-Butyl Ester;tert-butyl (2S,3R)-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)butanoate;O-(2-Azido-4,6-O-benzylidene-2-deoxy-|A-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-threonine tert-Butyl Ester;O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-threonine tert-Butyl Ester;DTXSID20693675;BPJMKNVMUZHIFM-HMAUQUTRSA-N;MFCD11112165;Fmoc-Thr[GalN3[46Bzd]-alpha]-OtBu;HY-W142098;CS-0201882;D88469;tert-Butyl (2S,3R)-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)butanoate (non-preferred name)

Chemical Property of O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-Fmoc-L-threonine tert-Butyl Ester

Chemical Property:

• PSA: 175.02000
• LogP: 5.17656
• Storage Temp.: <0°C
• XLogP3: 5.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 12
• Exact Mass: 672.27952887
• Heavy Atom Count: 49
• Complexity: 1170

Purity/Quality:

97% ^*data from raw suppliers

O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-threonine tert-Butyl Ester >97.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C(=O)OC(C)(C)C)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)OC4C(C(C5C(O4)COC(O5)C6=CC=CC=C6)O)N=[N+]=[N-]
• Isomeric SMILES: C[C@H]([C@@H](C(=O)OC(C)(C)C)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)O[C@@H]4[C@H]([C@H]([C@@H]5[C@@H](O4)COC(O5)C6=CC=CC=C6)O)N=[N+]=[N-]

Technology Process of O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-Fmoc-L-threonine tert-Butyl Ester

There total 3 articles about O-(2-Azido-4,6-O-benzylidene-2-deoxy-alpha-D-galactopyranosyl)-N-Fmoc-L-threonine 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: 76.0%

benzaldehyde dimethyl acetal (1125-88-8) + Nα-(9-fluorenylmethoxycarbony)-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-threonine tert-butyl ester (120173-56-0) → N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-(2-azido-2-deoxy-4,6-O-benzylidene-α-D-galactopyranosyl)-L-threonine tert-butyl ester (195976-07-9)

Guidance literature:

N^α-(9-fluorenylmethoxycarbony)-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-threonine tert-butyl ester; With sodium methylate; In methanol; at 25 ℃; for 1h;

benzaldehyde dimethyl acetal; With toluene-4-sulfonic acid; In acetonitrile; at 25 ℃; for 12h;

DOI:10.1002/cjoc.202100914

Reference yield: 65.0%

benzaldehyde dimethyl acetal (1125-88-8) + (2S,3R)-3-((2S,3R,4R,5R,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid tert-butyl ester (195976-26-2) → N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-(2-azido-2-deoxy-4,6-O-benzylidene-α-D-galactopyranosyl)-L-threonine tert-butyl ester (195976-07-9)

Guidance literature:

With toluene-4-sulfonic acid; In nitromethane; for 1h; Ambient temperature;

DOI:10.1039/a701742a

Reference yield:

N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-desoxy-α-D-galactopyranosyl)-1-threonine tert-butyl ester (120791-77-7) → N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-(2-azido-2-deoxy-4,6-O-benzylidene-α-D-galactopyranosyl)-L-threonine tert-butyl ester (195976-07-9)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol / 1 h

2: 65 percent / p-TsOH / nitromethane / 1 h / Ambient temperature

With sodium methylate; toluene-4-sulfonic acid; In methanol; nitromethane;

DOI:10.1039/a701742a

upstream raw materials:

benzaldehyde dimethyl acetal

(2S,3R)-3-((2S,3R,4R,5R,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid tert-butyl ester

N-(9H-fluoren-9-yl)-methoxycarbonyl-O-(3,4,6-tri-O-acetyl-2-azido-2-desoxy-α-D-galactopyranosyl)-1-threonine tert-butyl ester

N^α-(9-fluorenylmethoxycarbony)-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α-D-galactopyranosyl)-L-threonine tert-butyl ester

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-threonine tert-butyl ester

N^α-(fluoren-9-ylmethoxycarbonyl)-O-[O-[3',4',6'-tri-O-benzoyl-2'-deoxy-2'-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-(1'->3)]-2-azido-2-deoxy-α-D-galactopyranosyl]-L-threonine tert-butyl ester

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