(1R,2R,3S,4S,5S)-3-acetamido-2-benzyloxy-4-(benzyloxy)amino-5-[(benzyloxy)methyl]cyclopentyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: (1R,2R,3S,4S,5S)-3-acetamido-2-benzyloxy-4-(benzyloxy)amino-5-[(benzyloxy)methyl]cyclopentyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 175289-16-4
• Molecular Formula: C₅₈H₆₅N₃O₁₀
• Molecular Weight: 964.168

Synonyms:(1R,2R,3S,4S,5S)-3-acetamido-2-benzyloxy-4-(benzyloxy)amino-5-[(benzyloxy)methyl]cyclopentyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

Chemical Property of (1R,2R,3S,4S,5S)-3-acetamido-2-benzyloxy-4-(benzyloxy)amino-5-[(benzyloxy)methyl]cyclopentyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

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Technology Process of (1R,2R,3S,4S,5S)-3-acetamido-2-benzyloxy-4-(benzyloxy)amino-5-[(benzyloxy)methyl]cyclopentyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

There total 2 articles about (1R,2R,3S,4S,5S)-3-acetamido-2-benzyloxy-4-(benzyloxy)amino-5-[(benzyloxy)methyl]cyclopentyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside 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: 31.0%

Thiocarbonic acid O-[(2S,3R,4S)-4-acetylamino-2-((2S,3R,4R,5S,6R)-3-acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-3-benzyloxy-5-benzyloxyimino-1-benzyloxymethyl-pentyl] ester O-phenyl ester → (1R,2R,3S,4S,5R)-3-acetamido-2-benzyloxy-4-(benzyloxy)amino-5-[(benzyloxy)methyl]cyclopentyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside + (1R,2R,3S,4R,5R)-3-acetamido-2-benzyloxy-4-(benzyloxy)amino-5-[(benzyloxy)methyl]cyclopentyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside + (1R,2R,3S,4S,5S)-3-acetamido-2-benzyloxy-4-(benzyloxy)amino-5-[(benzyloxy)methyl]cyclopentyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (175289-16-4) + (1R,2R,3S,4R,5S)-3-acetamido-2-benzyloxy-4-(benzyloxy)amino-5-[(benzyloxy)methyl]cyclopentyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; at 100 - 110 ℃;

DOI:10.1246/cl.1996.97

Reference yield:

2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-5-O-phenoxy(thiocarbonyl)-D-glucose O-benzyl oxime → (1R,2R,3S,4S,5R)-3-acetamido-2-benzyloxy-4-(benzyloxy)amino-5-[(benzyloxy)methyl]cyclopentyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside + (1R,2R,3S,4R,5R)-3-acetamido-2-benzyloxy-4-(benzyloxy)amino-5-[(benzyloxy)methyl]cyclopentyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside + (1R,2R,3S,4S,5S)-3-acetamido-2-benzyloxy-4-(benzyloxy)amino-5-[(benzyloxy)methyl]cyclopentyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (175289-16-4) + (1R,2R,3S,4R,5S)-3-acetamido-2-benzyloxy-4-(benzyloxy)amino-5-[(benzyloxy)methyl]cyclopentyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

Guidance literature:

With triethyl borane; tri-n-butyl-tin hydride; In hexane; toluene; at 0 ℃; for 7h;

DOI:10.1016/S0040-4020(99)00972-2

Reference yield: 74.0%

(1R,2R,3S,4S,5S)-3-acetamido-2-benzyloxy-4-(benzyloxy)amino-5-[(benzyloxy)methyl]cyclopentyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (175289-16-4) + phenylcarbonochloridothioate (1005-56-7) → (1R,2R,3S,4S,5S)-3-acetamido-2-benzyloxy-4-(N-benzyloxy-N-phenoxythiocarbonyl)amino-5-[(benzyloxy)methyl]cyclopentyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside (175289-17-5)

Guidance literature:

With pyridine; In dichloromethane; Ambient temperature;

DOI:10.1246/cl.1996.97

Downstream raw materials:

(1R,2R,3S,4S,5S)-3-acetamido-2-benzyloxy-4-(N-benzyloxy-N-phenoxythiocarbonyl)amino-5-[(benzyloxy)methyl]cyclopentyl 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

(3aS,4R,5R,6S,6aS)-6-benzyloxymethyl-1,4-dibenzyloxy-2-thio-2,3,3a,5,6,6a-hexahydro-4H-cyclopentimidazole-5-yl acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

(3aS,4R,5R,6S,6aS)-4-benzyloxy-6-benzyloxymethyl-2-dimethylamino-3a,5,6,6a-tetrahydro-4H-cyclopentimidazole-5-yl acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

(3aS,4R,5R,6S,6aS)-4-benzyloxy-1,4-dibenzyloxy-2-dimethylamino-3a,5,6,6a-tetrahydro-4H-cyclopentimidazole-5-yl acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranoside

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