benzyl [N-benzyloxycarbonyl-3-amino-propyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-octulopyranosid] onate

Base Information

• Chemical Name: benzyl [N-benzyloxycarbonyl-3-amino-propyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-octulopyranosid] onate
• CAS No.: 1392224-71-3
• Molecular Formula: C₃₆H₄₃NO₁₀
• Molecular Weight: 649.738

Synonyms:benzyl [N-benzyloxycarbonyl-3-amino-propyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-octulopyranosid] onate

Chemical Property of benzyl [N-benzyloxycarbonyl-3-amino-propyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-octulopyranosid] onate

Chemical Property:

Purity/Quality:

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Technology Process of benzyl [N-benzyloxycarbonyl-3-amino-propyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-octulopyranosid] onate

There total 7 articles about benzyl [N-benzyloxycarbonyl-3-amino-propyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-octulopyranosid] onate 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: 84.0%

C29H37NO10 (1392224-74-6) + benzyl bromide (100-39-0) → benzyl [N-benzyloxycarbonyl-3-amino-propyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-octulopyranosid] onate (1392224-71-3)

Guidance literature:

C₂₉H₃₇NO₁₀; With methanol; di(n-butyl)tin oxide; for 3h; Inert atmosphere; Reflux;

benzyl bromide; With cesium fluoride; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/ja306274v

Reference yield:

benzyl [2-1,3-dithiane-3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate (1392224-88-2) → benzyl [N-benzyloxycarbonyl-3-amino-propyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-octulopyranosid] onate (1392224-71-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: water; N-Bromosuccinimide / acetone / 0.17 h / 0 °C / Inert atmosphere

2.1: diethylamino-sulfur trifluoride / dichloromethane / 0.25 h / -50 °C / Inert atmosphere; Molecular sieve

3.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / 0 °C / Inert atmosphere; Molecular sieve

4.1: water; acetic acid / 1 h / Inert atmosphere; Reflux

5.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide; 1,4-dioxane / 16 h / 20 °C / Inert atmosphere

6.1: di(n-butyl)tin oxide; methanol / 3 h / Inert atmosphere; Reflux

6.2: 16 h / 20 °C / Inert atmosphere

With methanol; N-Bromosuccinimide; diethylamino-sulfur trifluoride; boron trifluoride diethyl etherate; water; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ja306274v

Reference yield:

benzyl [3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate → benzyl [N-benzyloxycarbonyl-3-amino-propyl 4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-manno-octulopyranosid] onate (1392224-71-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: diethylamino-sulfur trifluoride / dichloromethane / 0.25 h / -50 °C / Inert atmosphere; Molecular sieve

2.1: boron trifluoride diethyl etherate / dichloromethane / 1 h / 0 °C / Inert atmosphere; Molecular sieve

3.1: water; acetic acid / 1 h / Inert atmosphere; Reflux

4.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide; 1,4-dioxane / 16 h / 20 °C / Inert atmosphere

5.1: di(n-butyl)tin oxide; methanol / 3 h / Inert atmosphere; Reflux

5.2: 16 h / 20 °C / Inert atmosphere

With methanol; diethylamino-sulfur trifluoride; boron trifluoride diethyl etherate; water; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja306274v

upstream raw materials:

benzyl [2-1,3-dithiane-3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate

benzyl [fluoro 3-deoxy-4,5-7,8-di-O-isopropylidene-α-D-manno-octulopyranosid]onate

C₂₉H₃₇NO₁₀

benzyl bromide

Downstream raw materials:

benzyl 3-O-acetyl-2-deoxy-2-(2,2,2-trichloroethyloxycarbonyl)-amino-4,6-O-(di-tert-butylsilanediyl)-α-D-galactosamine-(1→2)-4,6-di-O-benzylidene-3-O-(2-methylnaphthyl)-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-O-levulinoyl-α-D-mannopyranosyl-(1→5)-[N-benzyloxycarbonyl-3-amino-propyl-4-O-benzyl-3-deoxy-7,8-O-isopropylidene-α-D-mannooctulopyranosid]onate

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