(3E)-1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-5-amino-1,3,4,5-tetradeoxy-5-N-fluorenylmethoxycarbonyl-6-O-diphenyl-tert-butylsilyl-D-glycero-hex-3-eno-2-ulose

Base Information

• Chemical Name: (3E)-1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-5-amino-1,3,4,5-tetradeoxy-5-N-fluorenylmethoxycarbonyl-6-O-diphenyl-tert-butylsilyl-D-glycero-hex-3-eno-2-ulose
• CAS No.: 408359-37-5
• Molecular Formula: C₇₁H₇₃NO₉Si
• Molecular Weight: 1112.45
• Mol file: 408359-37-5.mol

Synonyms:(3E)-1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-5-amino-1,3,4,5-tetradeoxy-5-N-fluorenylmethoxycarbonyl-6-O-diphenyl-tert-butylsilyl-D-glycero-hex-3-eno-2-ulose

Chemical Property of (3E)-1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-5-amino-1,3,4,5-tetradeoxy-5-N-fluorenylmethoxycarbonyl-6-O-diphenyl-tert-butylsilyl-D-glycero-hex-3-eno-2-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3E)-1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-5-amino-1,3,4,5-tetradeoxy-5-N-fluorenylmethoxycarbonyl-6-O-diphenyl-tert-butylsilyl-D-glycero-hex-3-eno-2-ulose

There total 1 articles about (3E)-1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-5-amino-1,3,4,5-tetradeoxy-5-N-fluorenylmethoxycarbonyl-6-O-diphenyl-tert-butylsilyl-D-glycero-hex-3-eno-2-ulose 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: 86.0%

2-oxo-3-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)propylidenetriphenylphosphorane (124667-94-3) + O-diphenyl-tert-butyl-silyl-N-Fmoc-D-serinal → (3E)-1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-5-amino-1,3,4,5-tetradeoxy-5-N-fluorenylmethoxycarbonyl-6-O-diphenyl-tert-butylsilyl-D-glycero-hex-3-eno-2-ulose (408359-37-5)

Guidance literature:

In acetonitrile; for 20h;

DOI:10.1081/CAR-100108281

Reference yield: 85.0%

(3E)-1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-5-amino-1,3,4,5-tetradeoxy-5-N-fluorenylmethoxycarbonyl-6-O-diphenyl-tert-butylsilyl-D-glycero-hex-3-eno-2-ulose (408359-37-5) → [(R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2,3-dihydroxy-4-oxo-5-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-pentyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 20 - 40 ℃;

DOI:10.1081/CAR-100108281

Reference yield:

(3E)-1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-5-amino-1,3,4,5-tetradeoxy-5-N-fluorenylmethoxycarbonyl-6-O-diphenyl-tert-butylsilyl-D-glycero-hex-3-eno-2-ulose (408359-37-5) → 1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-3,4-di-O-acetyl-1,2,5-trideoxy-2,5-imino-6-O-diphenyl-tert-butylsilyl-D-manno-hexitol

Guidance literature:

Multi-step reaction with 3 steps

1.1: 85 percent / OsO₄; N-methylmorpholine-N-oxide / H₂O; acetone; 2-methyl-propan-2-ol / 20 - 40 °C

2.1: 46 percent / DMAP / CH₂Cl₂ / 0.08 h

3.1: piperidine / dimethylformamide / 0.5 h

3.2: 41 percent / Na₂SO₄; AcOH; NaBH(OAc)3 / CH₂Cl₂ / 4 h

With piperidine; dmap; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1081/CAR-100108281

upstream raw materials:

2-oxo-3-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)propylidenetriphenylphosphorane

Downstream raw materials:

1-C-(2,3,4,6-tetra-O-benzyl-(α-D-glucopyranosyl)-3,4-di-O-acetyl-5-amino-1,5-dideoxy-5-N-fluorenylmethoxycarbonyl-6-O-diphenyl-tert-butylsilyl-D-arabino-hex-2-ulose