1L-N¹-benzyloxycarbonyl-O⁶-[2-benzyloxycarbonylamino-O⁶-(toluene-4-sulfonyl)-α-D-ribo-2,3-dideoxy-hexopyranosyl]-O⁵-[O²,O⁵-bis-(4-nitro-benzoyl)-β-D-erythro-3-deoxy-pentofuranosyl]-N³,O⁴-carbonyl-2-deoxy-streptamine

Base Information

• Chemical Name: 1L-N¹-benzyloxycarbonyl-O⁶-[2-benzyloxycarbonylamino-O⁶-(toluene-4-sulfonyl)-α-D-ribo-2,3-dideoxy-hexopyranosyl]-O⁵-[O²,O⁵-bis-(4-nitro-benzoyl)-β-D-erythro-3-deoxy-pentofuranosyl]-N³,O⁴-carbonyl-2-deoxy-streptamine
• CAS No.: 68537-64-4
• Molecular Formula: C₅₅H₅₅N₅O₂₂S
• Molecular Weight: 1170.13

Synonyms:

Chemical Property of 1L-N¹-benzyloxycarbonyl-O⁶-[2-benzyloxycarbonylamino-O⁶-(toluene-4-sulfonyl)-α-D-ribo-2,3-dideoxy-hexopyranosyl]-O⁵-[O²,O⁵-bis-(4-nitro-benzoyl)-β-D-erythro-3-deoxy-pentofuranosyl]-N³,O⁴-carbonyl-2-deoxy-streptamine

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of 1L-N¹-benzyloxycarbonyl-O⁶-[2-benzyloxycarbonylamino-O⁶-(toluene-4-sulfonyl)-α-D-ribo-2,3-dideoxy-hexopyranosyl]-O⁵-[O²,O⁵-bis-(4-nitro-benzoyl)-β-D-erythro-3-deoxy-pentofuranosyl]-N³,O⁴-carbonyl-2-deoxy-streptamine

There total 4 articles about 1L-N¹-benzyloxycarbonyl-O⁶-[2-benzyloxycarbonylamino-O⁶-(toluene-4-sulfonyl)-α-D-ribo-2,3-dideoxy-hexopyranosyl]-O⁵-[O²,O⁵-bis-(4-nitro-benzoyl)-β-D-erythro-3-deoxy-pentofuranosyl]-N³,O⁴-carbonyl-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:

O2,O5-bis-(4-nitro-benzoyl)-β-D-erythro-3-deoxy-pentofuranosyl bromide (7057-29-6) → 1L-N1-benzyloxycarbonyl-O6-[2-benzyloxycarbonylamino-O6-(toluene-4-sulfonyl)-α-D-ribo-2,3-dideoxy-hexopyranosyl]-O5-[O2,O5-bis-(4-nitro-benzoyl)-β-D-erythro-3-deoxy-pentofuranosyl]-N3,O4-carbonyl-2-deoxy-streptamine (68537-64-4)

Guidance literature:

Multi-step reaction with 3 steps

1: Hg(CN)2 / CH₂Cl₂

2: aq. AcOH / dioxane

3: Py / 40 h / -20 °C

With pyridine; mercury(II) cyanide; acetic acid; In 1,4-dioxane; dichloromethane;

DOI:10.7164/antibiotics.31.933

Reference yield:

1L-N1-benzyloxycarbonyl-O6-(2-benzyloxycarbonylamino-O4,O6-cyclohexane-1,1-diyl-α-D-ribo-2,3-dideoxy-hexopyranosyl)-N3,O4-carbonyl-2-deoxy-streptamine (63604-34-2) → 1L-N1-benzyloxycarbonyl-O6-[2-benzyloxycarbonylamino-O6-(toluene-4-sulfonyl)-α-D-ribo-2,3-dideoxy-hexopyranosyl]-O5-[O2,O5-bis-(4-nitro-benzoyl)-β-D-erythro-3-deoxy-pentofuranosyl]-N3,O4-carbonyl-2-deoxy-streptamine (68537-64-4)

Guidance literature:

Multi-step reaction with 3 steps

1: Hg(CN)2 / CH₂Cl₂

2: aq. AcOH / dioxane

3: Py / 40 h / -20 °C

With pyridine; mercury(II) cyanide; acetic acid; In 1,4-dioxane; dichloromethane;

DOI:10.7164/antibiotics.31.933

Reference yield:

1L-N1-benzyloxycarbonyl-O6-(2-benzyloxycarbonylamino-O4,O6-cyclohexane-1,1-diyl-α-D-ribo-2,3-dideoxy-hexopyranosyl)-O5-[O2,O5-bis-(4-nitro-benzoyl)-β-D-erythro-3-deoxy-pentofuranosyl]-N3,O4-carbonyl-2-deoxy-streptamine (68537-62-2) → 1L-N1-benzyloxycarbonyl-O6-[2-benzyloxycarbonylamino-O6-(toluene-4-sulfonyl)-α-D-ribo-2,3-dideoxy-hexopyranosyl]-O5-[O2,O5-bis-(4-nitro-benzoyl)-β-D-erythro-3-deoxy-pentofuranosyl]-N3,O4-carbonyl-2-deoxy-streptamine (68537-64-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. AcOH / dioxane

2: Py / 40 h / -20 °C

With pyridine; acetic acid; In 1,4-dioxane;

DOI:10.7164/antibiotics.31.933

upstream raw materials:

1L-N¹-benzyloxycarbonyl-O⁶-(2-benzyloxycarbonylamino-α-D-ribo-2,3-dideoxy-hexopyranosyl)-O⁵-[O²,O⁵-bis-(4-nitro-benzoyl)-β-D-erythro-3-deoxy-pentofuranosyl]-N³,O⁴-carbonyl-2-deoxy-streptamine

p-toluenesulfonyl chloride

1L-N¹-benzyloxycarbonyl-O⁶-(2-benzyloxycarbonylamino-O⁴,O⁶-cyclohexane-1,1-diyl-α-D-ribo-2,3-dideoxy-hexopyranosyl)-N³,O⁴-carbonyl-2-deoxy-streptamine

O²,O⁵-bis-(4-nitro-benzoyl)-β-D-erythro-3-deoxy-pentofuranosyl bromide

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