3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2,3,6-trideoxy-4-O-(4-nitrobenzoyl)-3-[(trifluoroacetyl)amino]hexopyranoside

Base Information

• Chemical Name: 3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2,3,6-trideoxy-4-O-(4-nitrobenzoyl)-3-[(trifluoroacetyl)amino]hexopyranoside
• CAS No.: 76793-42-5
• Molecular Formula: C36H31 F3 N2 O14
• Molecular Weight: 772.6315
• Mol file: 76793-42-5.mol

Synonyms:NSC305992

Chemical Property of 3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2,3,6-trideoxy-4-O-(4-nitrobenzoyl)-3-[(trifluoroacetyl)amino]hexopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 920.9°Cat760mmHg
• Flash Point: 510.7°C
• Density: 1.61g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2,3,6-trideoxy-4-O-(4-nitrobenzoyl)-3-[(trifluoroacetyl)amino]hexopyranoside

There total 12 articles about 3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 2,3,6-trideoxy-4-O-(4-nitrobenzoyl)-3-[(trifluoroacetyl)amino]hexopyranoside 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: 50.0%

(+)-Daunomycinone (21794-55-8) + 1-O-acetyl-2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-L-xylo-hexopyranose (67279-09-8) → 7-O-(2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-L-xylo-hexopyranosyl)daunomycinone (76793-42-5)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; benzene; at 20 ℃; for 2h;

DOI:10.1016/S0008-6215(00)84673-X

Reference yield:

(+)-Daunomycinone (21794-55-8) + 2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-L-arabino-hex-1-enitol (73891-04-0) → 7-O-<2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-α-L-arabino-hexopyranosyl>daunomycinone (73926-01-9) + 7-O-<2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-(trifluoroacetamido)-β-L-arabino-hexopyranosyl>daunomycinone (52583-24-1,62445-20-9,70629-86-6,70629-87-7,72402-71-2,73926-01-9,76793-42-5,76793-44-7,76793-45-8,76793-59-4,98103-09-4)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; benzene; at 20 ℃; for 2.5h; Yield given. Yields of byproduct given;

DOI:10.1016/S0008-6215(00)83831-8

Reference yield:

methyl-2,3,6-tridesoxy-3-trifluoroacetamido-β-L-xylo-hexopyranoside (72002-53-0) → 7-O-(2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-L-xylo-hexopyranosyl)daunomycinone (76793-42-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / pyridine / 3 h / 0 °C

2: 86 percent / acetic acid / H₂O / 1.25 h / Heating

3: 80 percent / pyridine / 20 h / 25 °C

4: 50 percent / p-toluenesulfonic acid / benzene; CH₂Cl₂ / 2 h / 20 °C

With pyridine; toluene-4-sulfonic acid; acetic acid; In dichloromethane; water; benzene;

DOI:10.1016/S0008-6215(00)84673-X

upstream raw materials:

(+)-Daunomycinone

1-O-acetyl-2,3,6-tridesoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-α-L-xylo-hexopyranose

methyl-3-amino-2,3,6-tridesoxy-β-L-xylo-hexopyranoside

methyl-2,3,6-tridesoxy-3-trifluoroacetamido-β-L-xylo-hexopyranoside