2'-O-benzoyl-N,N-bis(benzyloxycarbonyl)-spectinomycin

Base Information

• Chemical Name: 2'-O-benzoyl-N,N-bis(benzyloxycarbonyl)-spectinomycin
• CAS No.: 866941-38-0
• Molecular Formula: C₃₇H₄₀N₂O₁₂
• Molecular Weight: 704.731
• Mol file: 866941-38-0.mol

Synonyms:2'-O-benzoyl-N,N-bis(benzyloxycarbonyl)-spectinomycin

Chemical Property of 2'-O-benzoyl-N,N-bis(benzyloxycarbonyl)-spectinomycin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-O-benzoyl-N,N-bis(benzyloxycarbonyl)-spectinomycin

There total 4 articles about 2'-O-benzoyl-N,N-bis(benzyloxycarbonyl)-spectinomycin 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: 51.0%

N,N'-<(benzyloxy)carbonyl>actinamine (64979-02-8) + (2R,6R)-2-chloro-4-benzoyloxy-6-methyl-2H-pyran-3-(6H)-one (88773-23-3) → 2'-O-benzoyl-N,N-bis(benzyloxycarbonyl)-spectinomycin (866941-38-0)

Guidance literature:

With silver alumosilicate; In toluene; at 80 ℃; for 3h;

DOI:10.1002/anie.200500434

Reference yield: 51.0%

N,N'-<(benzyloxy)carbonyl>actinamine (64979-02-8) + (2R,6R)-2-chloro-4-benzoyloxy-6-methyl-2H-pyran-3-(6H)-one (88773-23-3) → 2'-O-benzoyl-N,N-bis(benzyloxycarbonyl)-spectinomycin (866941-38-0) + Benzoic acid (R)-2-[(1S,2R,3R,4S,5R,6S)-2,4-bis-(benzyloxycarbonyl-methyl-amino)-3,5,6-trihydroxy-cyclohexyloxy]-6-methyl-3-oxo-3,6-dihydro-2H-pyran-4-yl ester + Benzoic acid (R)-2-[(1R,2S,3S,4R,5S,6R)-2,4-bis-(benzyloxycarbonyl-methyl-amino)-3,5,6-trihydroxy-cyclohexyloxy]-6-methyl-3-oxo-3,6-dihydro-2H-pyran-4-yl ester

Guidance literature:

N,N'-<(benzyloxy)carbonyl>actinamine; With 4 A molecular sieve; silver alumosilicate reagent; In toluene; at 25 ℃; for 0.25h;

(2R,6R)-2-chloro-4-benzoyloxy-6-methyl-2H-pyran-3-(6H)-one; In toluene; at 80 ℃; for 2.5h;

DOI:10.1016/j.tetasy.2006.03.035

Reference yield:

1,5-anhydro-2,3,4-tri-O-benzoyl-6-deoxy-D-arabino-hex-1-enitol (52080-34-9) → 2'-O-benzoyl-N,N-bis(benzyloxycarbonyl)-spectinomycin (866941-38-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: chlorine / H₂O; toluene / -20 - 25 °C

1.2: 61 percent / NaHCO₃ / benzene; H₂O / 1.5 h / Heating

2.1: 74 percent / acetyl chloride; HCl / 12 h / 25 °C

3.1: molecular sieves 4 Angstroem; silver alumosilicate reagent / toluene / 0.25 h / 25 °C

3.2: 51 percent / toluene / 2.5 h / 80 °C

With hydrogenchloride; 4 A molecular sieve; silver alumosilicate reagent; chlorine; acetyl chloride; In water; toluene;

DOI:10.1016/j.tetasy.2006.03.035

upstream raw materials:

N,N'-<(benzyloxy)carbonyl>actinamine

(2R,6R)-2-chloro-4-benzoyloxy-6-methyl-2H-pyran-3-(6H)-one

1,5-anhydro-2,3,4-tri-O-benzoyl-6-deoxy-D-arabino-hex-1-enitol

(2S,6R)-2,4-bis(benzoyloxy)-6-methyl-2H-pyran-3(6H)-one

Downstream raw materials:

spectinomycin

1,3-bis(N-benzyloxycarbonyl)-spectinomycin

Refernces

• 1、 Lichtenthaler, Frieder W.,Cuny, Eckehard,Sakanaka, Osamu. "A concise and general method for doubly attaching 2-ketosugars to aglycon diols: Synthesis of the gomphosides and spectinomycin". . p. 4944 - 4948. Retrieved 2007/10/03.