O⁴-(6-amino-2-benzyloxycarbonylamino-N⁶,O⁴-carbonyl-O³-(Ξ)-tetrahydropyran-2-yl-α-D-2,6-dideoxy-glucopyranosyl)-N³-benzyloxycarbonyl-N¹,O⁶-carbonyl-1D-2-deoxy-streptamine

Base Information

• Chemical Name: O⁴-(6-amino-2-benzyloxycarbonylamino-N⁶,O⁴-carbonyl-O³-(Ξ)-tetrahydropyran-2-yl-α-D-2,6-dideoxy-glucopyranosyl)-N³-benzyloxycarbonyl-N¹,O⁶-carbonyl-1D-2-deoxy-streptamine
• CAS No.: 66787-83-5
• Molecular Formula: C₃₅H₄₂N₄O₁₃
• Molecular Weight: 726.737

Synonyms:O⁴-(6-amino-2-benzyloxycarbonylamino-N⁶,O⁴-carbonyl-O³-(Ξ)-tetrahydropyran-2-yl-α-D-2,6-dideoxy-glucopyranosyl)-N³-benzyloxycarbonyl-N¹,O⁶-carbonyl-1D-2-deoxy-streptamine

Chemical Property of O⁴-(6-amino-2-benzyloxycarbonylamino-N⁶,O⁴-carbonyl-O³-(Ξ)-tetrahydropyran-2-yl-α-D-2,6-dideoxy-glucopyranosyl)-N³-benzyloxycarbonyl-N¹,O⁶-carbonyl-1D-2-deoxy-streptamine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of O⁴-(6-amino-2-benzyloxycarbonylamino-N⁶,O⁴-carbonyl-O³-(Ξ)-tetrahydropyran-2-yl-α-D-2,6-dideoxy-glucopyranosyl)-N³-benzyloxycarbonyl-N¹,O⁶-carbonyl-1D-2-deoxy-streptamine

There total 2 articles about O⁴-(6-amino-2-benzyloxycarbonylamino-N⁶,O⁴-carbonyl-O³-(Ξ)-tetrahydropyran-2-yl-α-D-2,6-dideoxy-glucopyranosyl)-N³-benzyloxycarbonyl-N¹,O⁶-carbonyl-1D-2-deoxy-streptamine 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:

N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine (22854-75-7) → O4-(6-amino-2-benzyloxycarbonylamino-N6,O4-carbonyl-O3-(Ξ)-tetrahydropyran-2-yl-α-D-2,6-dideoxy-glucopyranosyl)-N3-benzyloxycarbonyl-N1,O6-carbonyl-1D-2-deoxy-streptamine (66787-83-5)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / dimethylformamide

2: TsOH / dimethylformamide

With sodium hydride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jo00411a014

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) + 3,2'-di-N-benzyloxycarbonyl-1,6:6',4'-N,O-carbonyl-neamine (66787-82-4) → O4-(6-amino-2-benzyloxycarbonylamino-N6,O4-carbonyl-O3-(Ξ)-tetrahydropyran-2-yl-α-D-2,6-dideoxy-glucopyranosyl)-N3-benzyloxycarbonyl-N1,O6-carbonyl-1D-2-deoxy-streptamine (66787-83-5)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1021/jo00411a014

Reference yield: 58.0%

O4-(6-amino-2-benzyloxycarbonylamino-N6,O4-carbonyl-O3-(Ξ)-tetrahydropyran-2-yl-α-D-2,6-dideoxy-glucopyranosyl)-N3-benzyloxycarbonyl-N1,O6-carbonyl-1D-2-deoxy-streptamine (66787-83-5) + 2,3,5-tri-O-acetyl-D-4-thioribofuranosyl chloride (59042-15-8) → 3,2'-Di-N-(benzyloxycarbonyl)-3'-O-(tetrahydropyranyl)-2'',3'',5''-tri-O-acetyl-1,6:6',4'-N,O-carbonylthioribostamycin (78763-86-7)

Guidance literature:

With calcium sulfate; mercury(II) cyanide; In dichloromethane; for 96h; Heating;

DOI:10.1021/jo00334a042

upstream raw materials:

3,4-dihydro-2H-pyran

3,2'-di-N-benzyloxycarbonyl-1,6:6',4'-N,O-carbonyl-neamine

N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine

Downstream raw materials:

O⁴-(6-amino-2-benzyloxycarbonylamino-N⁶,O⁴-carbonyl-O³-(Ξ)-tetrahydropyran-2-yl-α-D-2,6-dideoxy-glucopyranosyl)-N³-benzyloxycarbonyl-N¹,O⁶-carbonyl-O⁵-(tri-O-benzoyl-β-D-ribofuranosyl)-1D-2-deoxy-streptamine

3,2'-Di-N-(benzyloxycarbonyl)-3'-O-(tetrahydropyranyl)-2'',3'',5''-tri-O-acetyl-1,6:6',4'-N,O-carbonylthioribostamycin

4''-Thioribostamycin

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