methyl 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranoside

Base Information

• Chemical Name: methyl 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranoside
• CAS No.: 1381871-26-6
• Molecular Formula: C₄₂H₄₆O₉S
• Molecular Weight: 726.888

Synonyms:methyl 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranoside

Chemical Property of methyl 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranoside

There total 4 articles about methyl 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranoside 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: 76.0%

methanol (67-56-1) + ethyl 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-2-thio-α-D-gluco-hept-2-ulopyranoside (1381871-18-6) → methyl 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranoside (1381871-26-6) + methyl 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-β-D-gluco-hept-2-ulopyranoside (1381871-27-7)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In tetrahydrofuran; dichloromethane; at -20 ℃; for 0.333333h; optical yield given as %de; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tet.2012.04.067

Reference yield:

2,3,6-tri-O-benzyl-4-O-((2-naphthyl)methyl)-α,β-D-glucopyranose → methyl 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranoside (1381871-26-6) + methyl 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-β-D-gluco-hept-2-ulopyranoside (1381871-27-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h / -60 °C / Inert atmosphere

2.2: 3 h / -78 - -60 °C / Inert atmosphere

2.3: Inert atmosphere

3.1: boron trifluoride diethyl etherate / dichloromethane / 0 °C / Inert atmosphere

4.1: N-iodo-succinimide; trifluorormethanesulfonic acid / tetrahydrofuran; dichloromethane / 0.33 h / -20 °C / Inert atmosphere; Molecular sieve

With N-iodo-succinimide; n-butyllithium; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1.1: Dess-Martin oxidation;

DOI:10.1016/j.tet.2012.04.067

Reference yield:

2,3,6-tri-O-benzyl-4-O-((2-naphthyl)methyl)-D-glucono-1,5-lactone (1381871-15-3) → methyl 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranoside (1381871-26-6) + methyl 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-β-D-gluco-hept-2-ulopyranoside (1381871-27-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.25 h / -60 °C / Inert atmosphere

1.2: 3 h / -78 - -60 °C / Inert atmosphere

1.3: Inert atmosphere

2.1: boron trifluoride diethyl etherate / dichloromethane / 0 °C / Inert atmosphere

3.1: N-iodo-succinimide; trifluorormethanesulfonic acid / tetrahydrofuran; dichloromethane / 0.33 h / -20 °C / Inert atmosphere; Molecular sieve

With N-iodo-succinimide; n-butyllithium; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2012.04.067

upstream raw materials:

methanol

ethyl 3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-2-thio-α-D-gluco-hept-2-ulopyranoside

2,3,6-tri-O-benzyl-4-O-((2-naphthyl)methyl)-D-glucono-1,5-lactone

3,4,7-tri-O-benzyl-5-O-((2-naphthyl)methyl)-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranose

Downstream raw materials:

methyl 3,4,7-tri-O-benzyl-1-deoxy-1-ethoxysulfonyl-α-D-gluco-hept-2-ulopyranoside

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