(2S,3S,5R)-3-Azido-2-benzoyloxy-5-<3'-azido-4'-O-p-nitrobenzoyl-2',3',6'-trideoxy-α-L-arabino-hexopyranosyloxy>cyclohexanone ethylene dithioacetal

Base Information

• Chemical Name: (2S,3S,5R)-3-Azido-2-benzoyloxy-5-<3'-azido-4'-O-p-nitrobenzoyl-2',3',6'-trideoxy-α-L-arabino-hexopyranosyloxy>cyclohexanone ethylene dithioacetal
• CAS No.: 171074-41-2
• Molecular Formula: C₂₈H₂₉N₇O₈S₂
• Molecular Weight: 655.712
• Mol file: 171074-41-2.mol

Synonyms:

Chemical Property of (2S,3S,5R)-3-Azido-2-benzoyloxy-5-<3'-azido-4'-O-p-nitrobenzoyl-2',3',6'-trideoxy-α-L-arabino-hexopyranosyloxy>cyclohexanone ethylene dithioacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5R)-3-Azido-2-benzoyloxy-5-<3'-azido-4'-O-p-nitrobenzoyl-2',3',6'-trideoxy-α-L-arabino-hexopyranosyloxy>cyclohexanone ethylene dithioacetal

There total 2 articles about (2S,3S,5R)-3-Azido-2-benzoyloxy-5-<3'-azido-4'-O-p-nitrobenzoyl-2',3',6'-trideoxy-α-L-arabino-hexopyranosyloxy>cyclohexanone ethylene dithioacetal 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: 7.0%

3-Azido-1,4-di-O-(p-nitrobenzoyl)-2,3,6-trideoxy-α,β-L-arabino-hexopyranose (149055-63-0) + (2S,3R,5R)-3-Azido-2-benzoyloxy-5-hydroxycyclohexanone ethylene dithioacetal (171074-26-3) → (2S,3S,5R)-3-Azido-2-benzoyloxy-5-<3'-azido-4'-O-p-nitrobenzoyl-2',3',6'-trideoxy-α-L-arabino-hexopyranosyloxy>cyclohexanone ethylene dithioacetal (171074-41-2) + (2S,3S,5R)-3-Azido-2-benzoyloxy-5-<3'-azido-4'-O-p-nitrobenzoyl-2',3',6'-trideoxy-β-L-arabino-hexopyranosyloxy>cyclohexanone ethylene dithioacetal

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In dichloromethane; 1.) 2 h, 2.) -20 deg C, 3 d;

DOI:10.7164/antibiotics.48.683

Reference yield:

(2S,3R,5R)-3-Azido-2-benzoyloxy-5-hydroxycyclohexanone (90146-07-9) → (2S,3S,5R)-3-Azido-2-benzoyloxy-5-<3'-azido-4'-O-p-nitrobenzoyl-2',3',6'-trideoxy-α-L-arabino-hexopyranosyloxy>cyclohexanone ethylene dithioacetal (171074-41-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / BF₃*Et₂O / CH₂Cl₂

2: trimethylsilyl triflate, 4 A molecular sieves / CH₂Cl₂

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/0008-6215(95)00130-L

Reference yield:

(2S,3S,5R)-3-Azido-2-benzoyloxy-5-<3'-azido-4'-O-p-nitrobenzoyl-2',3',6'-trideoxy-α-L-arabino-hexopyranosyloxy>cyclohexanone ethylene dithioacetal (171074-41-2) → (1R,2R,4S)-2-Amino-1-hydroxy-4-(3'-amino-2',3',6'-trideoxy-α-L-arabino-hexopyranosyloxy)cyclohexane

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NaOCH₃ / methanol

2: 62.5 percent / hydrogen / Raney nickel / methanol

With hydrogen; sodium methylate; nickel; In methanol;

DOI:10.1016/0008-6215(95)00130-L

upstream raw materials:

3-Azido-1,4-di-O-(p-nitrobenzoyl)-2,3,6-trideoxy-α,β-L-arabino-hexopyranose

(2S,3R,5R)-3-Azido-2-benzoyloxy-5-hydroxycyclohexanone ethylene dithioacetal

(2S,3R,5R)-3-Azido-2-benzoyloxy-5-hydroxycyclohexanone