O⁴-[6-amino-2-benzyloxycarbonylamino-N⁶,O⁴-carbonyl-O³-(toluene-4-sulfonyl)-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-(toluene-4-sulfonyl)-α-D-2,6-dideoxy-glucopyranosyl]-N³-benzyloxycarbonyl-N¹,O⁶-carbonyl-1D-2-deoxy-streptamine
• CAS No.: 66787-84-6
• Molecular Formula: C₃₇H₄₀N₄O₁₄S
• Molecular Weight: 796.809

Synonyms:O⁴-[6-amino-2-benzyloxycarbonylamino-N⁶,O⁴-carbonyl-O³-(toluene-4-sulfonyl)-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-(toluene-4-sulfonyl)-α-D-2,6-dideoxy-glucopyranosyl]-N³-benzyloxycarbonyl-N¹,O⁶-carbonyl-1D-2-deoxy-streptamine

Chemical Property:

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Technology Process of O⁴-[6-amino-2-benzyloxycarbonylamino-N⁶,O⁴-carbonyl-O³-(toluene-4-sulfonyl)-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-(toluene-4-sulfonyl)-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-(toluene-4-sulfonyl)-α-D-2,6-dideoxy-glucopyranosyl]-N3-benzyloxycarbonyl-N1,O6-carbonyl-1D-2-deoxy-streptamine (66787-84-6)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / dimethylformamide

2: Py

With pyridine; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1021/jo00411a014

Reference yield:

3,2'-di-N-benzyloxycarbonyl-1,6:6',4'-N,O-carbonyl-neamine (66787-82-4) + p-toluenesulfonyl chloride (98-59-9) → O4-[6-amino-2-benzyloxycarbonylamino-N6,O4-carbonyl-O3-(toluene-4-sulfonyl)-α-D-2,6-dideoxy-glucopyranosyl]-N3-benzyloxycarbonyl-N1,O6-carbonyl-1D-2-deoxy-streptamine (66787-84-6)

Guidance literature:

With pyridine;

DOI:10.1021/jo00411a014

Reference yield: 72.0%

O4-[6-amino-2-benzyloxycarbonylamino-N6,O4-carbonyl-O3-(toluene-4-sulfonyl)-α-D-2,6-dideoxy-glucopyranosyl]-N3-benzyloxycarbonyl-N1,O6-carbonyl-1D-2-deoxy-streptamine (66787-84-6) → 2',3'-dideoxy-2',3'--3-N-(benzyloxycarbonyl)-1,6:6',4'-N,O-dicarbonylenamine (72163-39-4)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 25 ℃; for 24h;

DOI:10.1021/jm00175a009

upstream raw materials:

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

p-toluenesulfonyl chloride

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

Downstream raw materials:

2',3'-dideoxy-2',3'--3-N-(benzyloxycarbonyl)-1,6:6',4'-N,O-dicarbonylenamine

2',3'-dideoxy-2',3'-epimo-3-N-(benzyloxycarbonyl)neamine

2',3'-epiminoneamine

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