2-O-benzyl-6-N-benzyl-6-tosylamido-3,5,6-trideoxy-L-erythro-hexofuranosyl chloride

Base Information

• Chemical Name: 2-O-benzyl-6-N-benzyl-6-tosylamido-3,5,6-trideoxy-L-erythro-hexofuranosyl chloride
• CAS No.: 316804-42-9
• Molecular Formula: C₂₇H₃₀ClNO₄S
• Molecular Weight: 500.058

Synonyms:2-O-benzyl-6-N-benzyl-6-tosylamido-3,5,6-trideoxy-L-erythro-hexofuranosyl chloride

Chemical Property of 2-O-benzyl-6-N-benzyl-6-tosylamido-3,5,6-trideoxy-L-erythro-hexofuranosyl chloride

Chemical Property:

Purity/Quality:

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Technology Process of 2-O-benzyl-6-N-benzyl-6-tosylamido-3,5,6-trideoxy-L-erythro-hexofuranosyl chloride

There total 2 articles about 2-O-benzyl-6-N-benzyl-6-tosylamido-3,5,6-trideoxy-L-erythro-hexofuranosyl chloride 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: 100.0%

2-O-benzyl-6-N-benzyl-6-tosylamido-3,5,6-trideoxy-L-erythro-hexofuranose → 2-O-benzyl-6-N-benzyl-6-tosylamido-3,5,6-trideoxy-L-erythro-hexofuranosyl chloride (316804-42-9)

Guidance literature:

With thionyl chloride; at 20 ℃; for 3h;

DOI:10.1016/S0008-6215(00)00184-1

Reference yield:

methyl 2-O-benzyl-6-N-benzyl-6-tosylamido-3,5,6-trideoxy-L-erythro-hexofuranoside → 2-O-benzyl-6-N-benzyl-6-tosylamido-3,5,6-trideoxy-L-erythro-hexofuranosyl chloride (316804-42-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / aq. HCl; aq. AcOH / 6 h / 20 °C

2: 100 percent / SOCl₂ / 3 h / 20 °C

With hydrogenchloride; thionyl chloride; acetic acid;

DOI:10.1016/S0008-6215(00)00184-1

Reference yield:

2-O-benzyl-6-N-benzyl-6-tosylamido-3,5,6-trideoxy-L-erythro-hexofuranosyl chloride (316804-42-9) + 6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine (316804-48-5) → 6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-4-O-(2-O-benzyl-6-N-benzyl-6-tosylamido-3,5,6-trideoxy-α-L-erythro-hexofuranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine + 6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-4-O-(2-O-benzyl-6-N-benzyl-6-tosylamido-3,5,6-trideoxy-β-L-erythro-hexofuranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine (316804-56-5)

Guidance literature:

With 2,4,6-trimethyl-pyridine; mercury(II) cyanide; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1016/S0008-6215(00)00184-1

Downstream raw materials:

6-O-(2-O-acetyl-4,6-O-benzylidene-3-deoxy-3-tosylamido-α-D-glucopyranosyl)-4-O-(2-O-benzyl-6-N-benzyl-6-tosylamido-3,5,6-trideoxy-β-L-erythro-hexofuranosyl)-2,5-dideoxy-5-epi-5-fluoro-1,3-di-N-tosylstreptamine

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