1,3-di-N-benzyl-5,6-O-cyclohexylidene-2-deoxy-4-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-1,3-di-N-methoxycarbonylstreptamine

Base Information

• Chemical Name: 1,3-di-N-benzyl-5,6-O-cyclohexylidene-2-deoxy-4-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-1,3-di-N-methoxycarbonylstreptamine
• CAS No.: 110537-72-9
• Molecular Formula: C₄₀H₅₀N₂O₁₂
• Molecular Weight: 750.843
• Mol file: 110537-72-9.mol

Synonyms:1,3-di-N-benzyl-5,6-O-cyclohexylidene-2-deoxy-4-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-1,3-di-N-methoxycarbonylstreptamine

Chemical Property of 1,3-di-N-benzyl-5,6-O-cyclohexylidene-2-deoxy-4-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-1,3-di-N-methoxycarbonylstreptamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3-di-N-benzyl-5,6-O-cyclohexylidene-2-deoxy-4-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-1,3-di-N-methoxycarbonylstreptamine

There total 6 articles about 1,3-di-N-benzyl-5,6-O-cyclohexylidene-2-deoxy-4-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-1,3-di-N-methoxycarbonylstreptamine 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: 75.0%

1,3-di-N-benzyl-5,6-O-cyclohexylidene-2-deoxy-1,3-di-N-methoxycarbonylstreptamine (66266-01-1,73068-63-0) + D-glucal triacetate (2873-29-2) → 1,3-di-N-benzyl-5,6-O-cyclohexylidene-2-deoxy-4-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-1,3-di-N-methoxycarbonylstreptamine (110537-72-9)

Guidance literature:

With boron trifluoride diethyl etherate; triethylamine; In chloroform; at -5 ℃; for 2h;

DOI:10.1016/S0008-6215(00)90217-9

Reference yield:

3',4':5,6-di-O-cyclohexylidene-tetra-N-methoxycarbonylneamine (82472-81-9) → 1,3-di-N-benzyl-5,6-O-cyclohexylidene-2-deoxy-4-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-1,3-di-N-methoxycarbonylstreptamine (110537-72-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 83 percent / sodium hydride, N,N-dimethylformamide / 24 h / 25 °C

2: 81 percent / 1:1 acetic acid / 7 h / 56 °C

3: periodic acid / tetrahydrofuran / 1 h

4: 0.15 g / triethylamine / methanol / 24 h / 25 °C

5: 81 percent / sodium methoxide / methanol / 2 h / 70 °C

6: 75 percent / boron trifluoride etherate, triethylamine / CHCl₃ / 2 h / -5 °C

With boron trifluoride diethyl etherate; sodium methylate; sodium hydride; acetic acid; periodic acid; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; chloroform;

DOI:10.1016/S0008-6215(00)90217-9

Reference yield:

tetra-N-benzyl-3',4':5,6-di-O-cyclohexylidene-tetra-N-methoxycarbonylneamine (110537-69-4) → 1,3-di-N-benzyl-5,6-O-cyclohexylidene-2-deoxy-4-O-(4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)-1,3-di-N-methoxycarbonylstreptamine (110537-72-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / 1:1 acetic acid / 7 h / 56 °C

2: periodic acid / tetrahydrofuran / 1 h

3: 0.15 g / triethylamine / methanol / 24 h / 25 °C

4: 81 percent / sodium methoxide / methanol / 2 h / 70 °C

5: 75 percent / boron trifluoride etherate, triethylamine / CHCl₃ / 2 h / -5 °C

With boron trifluoride diethyl etherate; sodium methylate; acetic acid; periodic acid; triethylamine; In tetrahydrofuran; methanol; chloroform;

DOI:10.1016/S0008-6215(00)90217-9

upstream raw materials:

1,3-di-N-benzyl-5,6-O-cyclohexylidene-2-deoxy-1,3-di-N-methoxycarbonylstreptamine

D-glucal triacetate

1L-N¹,N³-dibenzyl-N¹,O⁶-carbonyl-O⁴,O⁵-cyclohexane-1,1-diyl-N³-methoxycarbonyl-2-deoxy-streptamine

3',4':5,6-di-O-cyclohexylidene-tetra-N-methoxycarbonylneamine

Downstream raw materials:

1,3-di-N-benzyl-5,6-O-cyclohexylidene-2-deoxy-4-O-(2,3-dideoxy-α-D-erythro-hexopyranosyl)-1,3-di-N-methoxycarbonylstreptamine

1,3-di-N-benzyl-1,3-di-N-benzyloxycarbonyl-4-O-<6-benzyloxycarbonylamino-4-O-(6-benzyloxycarbonylamino-2,3,6-trideoxy-α-D-erythro-hexopyranosyl)-2,3,6-trideoxy-α-D-erythro-hexopyranosyl>-5,6-O-cyclohexylidene-2-deoxystreptamine

4-O-<6-amino-4-O-(6-amino-2,3,6-trideoxy-α-D-erythro-hexopyranosyl)-2.3.6-trideoxy-α-D-erythro-hexopyranosyl>-2-deoxystreptamine tetrahydrochloride

4-O-(6-amino-2,3,6-trideoxy-α-D-erythro-hexopyranosyl)-1,3-di-N-benzyl-5,6-O-cyclohexylidene-2-deoxystreptamine