methyl (methyl 4-deoxy-2,3-di-O-methyl-α-L-threo-hex-4-enopyranosyluronate)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-C-(sodium sulfonatomethyl)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl (methyl 4-deoxy-2,3-di-O-methyl-α-L-threo-hex-4-enopyranosyluronate)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-C-(sodium sulfonatomethyl)-α-D-glucopyranoside
• CAS No.: 1333164-19-4
• Molecular Formula: C₃₁H₃₉O₁₃S*Na
• Molecular Weight: 674.699

Synonyms:methyl (methyl 4-deoxy-2,3-di-O-methyl-α-L-threo-hex-4-enopyranosyluronate)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-C-(sodium sulfonatomethyl)-α-D-glucopyranoside

Chemical Property of methyl (methyl 4-deoxy-2,3-di-O-methyl-α-L-threo-hex-4-enopyranosyluronate)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-C-(sodium sulfonatomethyl)-α-D-glucopyranoside

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Technology Process of methyl (methyl 4-deoxy-2,3-di-O-methyl-α-L-threo-hex-4-enopyranosyluronate)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-C-(sodium sulfonatomethyl)-α-D-glucopyranoside

There total 4 articles about methyl (methyl 4-deoxy-2,3-di-O-methyl-α-L-threo-hex-4-enopyranosyluronate)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-C-(sodium sulfonatomethyl)-α-D-glucopyranoside 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:

C31H42O14S (1161723-66-5) + methyl iodide (74-88-4) → methyl (methyl 4-deoxy-2,3-di-O-methyl-α-L-threo-hex-4-enopyranosyluronate)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-C-(sodium sulfonatomethyl)-α-D-glucopyranoside (1333164-19-4) + methyl (methyl 2,3,4-tri-O-methyl-α-L-idopyranosyluronate)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-C-(sodium sulfonatomethyl)-α-D-glucopyranoside (1333164-18-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2h;

DOI:10.1016/j.carres.2011.06.021

Reference yield:

C14H20O10 → methyl (methyl 4-deoxy-2,3-di-O-methyl-α-L-threo-hex-4-enopyranosyluronate)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-C-(sodium sulfonatomethyl)-α-D-glucopyranoside (1333164-19-4) + methyl (methyl 2,3,4-tri-O-methyl-α-L-idopyranosyluronate)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-C-(sodium sulfonatomethyl)-α-D-glucopyranoside (1333164-18-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: benzylamine / tetrahydrofuran / 4 h

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 0 °C

3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.25 h / -20 - 0 °C / Molecular sieve

3.2: 2 h / 20 °C

4.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; benzylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2011.06.021

Reference yield:

methyl 2,4-di-O-acetyl-3-O-methyl-L-idopyranosyluronate → methyl (methyl 4-deoxy-2,3-di-O-methyl-α-L-threo-hex-4-enopyranosyluronate)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-C-(sodium sulfonatomethyl)-α-D-glucopyranoside (1333164-19-4) + methyl (methyl 2,3,4-tri-O-methyl-α-L-idopyranosyluronate)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-C-(sodium sulfonatomethyl)-α-D-glucopyranoside (1333164-18-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 0 °C

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.25 h / -20 - 0 °C / Molecular sieve

2.2: 2 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C

With trimethylsilyl trifluoromethanesulfonate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.carres.2011.06.021

upstream raw materials:

C₁₄H₁₈Cl₃NO₉

C₃₁H₄₂O₁₄S

methyl iodide

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