2',3'-anhydro-1,3,6',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3'-epikanamycin A

Base Information

Chemical Name:2',3'-anhydro-1,3,6',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3'-epikanamycin A
CAS No.:139978-76-0
Molecular Formula:C₅₆H₆₆N₄O₁₈
Molecular Weight:1083.16
Hs Code.:

Synonyms:2',3'-anhydro-1,3,6',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3'-epikanamycin A

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Chemical Property of 2',3'-anhydro-1,3,6',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3'-epikanamycin A

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Technology Process of 2',3'-anhydro-1,3,6',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3'-epikanamycin A

There total 7 articles about 2',3'-anhydro-1,3,6',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3'-epikanamycin A 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: 91.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 139978-75-9
2',3'-anhydro-4'',6''-O-cyclohexylidene-3'-epikanamycin A

: 139978-76-0
2',3'-anhydro-1,3,6',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3'-epikanamycin A

Guidance literature:: With sodium carbonate; In 1,4-dioxane; water; at 0 - 5 ℃; for 3h;
DOI:10.1016/0008-6215(92)84101-W

Reference yield:

: 76550-53-3
6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-1,3,3''-tri-N-tosylkanamycin A

: 139978-76-0
2',3'-anhydro-1,3,6',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3'-epikanamycin A

Guidance literature:: Multi-step reaction with 7 steps

1: 90 percent / pyridine, 5percent NaHCO₃ / dimethylsulfoxide; H₂O / Ambient temperature

2: 88 mg / pyridine / 0.17 h / 0 - 5 °C

3: 88 percent / Zemplen deacetylation

4: 89 percent / phenylmethanol / 0.01 h / 45 °C

5: Na, liquid NH₃ / 1.) -50 deg C, 5 min 2.) MeOH, -50 deg C -> rt

6: Dowex 50W-X₂ (H⁽¹⁺⁾)form / H₂O / 0.25 h / 50 °C

7: 91 percent / Na₂CO₃ / dioxane; H₂O / 3 h / 0 - 5 °C

With pyridine; Dowex 50W-X₂ (H⁽¹⁺⁾)form; ammonia; sodium; sodium hydrogencarbonate; sodium carbonate; In 1,4-dioxane; water; dimethyl sulfoxide; benzyl alcohol;
DOI:10.1016/0008-6215(92)84101-W

Reference yield:

: 107009-76-7
2',2''-di-O-acetyl-3'-O-benzylsulfonyl-6'-N,4'-O-carbonyl-4'',6''-O-cyclohexylidene-1,3,3''-tri-N-tosylkanamycin A

: 139978-76-0
2',3'-anhydro-1,3,6',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3'-epikanamycin A

Guidance literature:: Multi-step reaction with 5 steps

1: 88 percent / Zemplen deacetylation

2: 89 percent / phenylmethanol / 0.01 h / 45 °C

3: Na, liquid NH₃ / 1.) -50 deg C, 5 min 2.) MeOH, -50 deg C -> rt

4: Dowex 50W-X₂ (H⁽¹⁺⁾)form / H₂O / 0.25 h / 50 °C

5: 91 percent / Na₂CO₃ / dioxane; H₂O / 3 h / 0 - 5 °C

With Dowex 50W-X₂ (H⁽¹⁺⁾)form; ammonia; sodium; sodium carbonate; In 1,4-dioxane; water; benzyl alcohol;
DOI:10.1016/0008-6215(92)84101-W