methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2,3-di-O-methyl-5-C-ethyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2,3-di-O-methyl-5-C-ethyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside
• CAS No.: 229956-33-6
• Molecular Formula: C₄₅H₅₄O₁₂
• Molecular Weight: 786.917

Synonyms:methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2,3-di-O-methyl-5-C-ethyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside

Chemical Property of methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2,3-di-O-methyl-5-C-ethyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

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Technology Process of methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2,3-di-O-methyl-5-C-ethyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside

There total 9 articles about methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2,3-di-O-methyl-5-C-ethyl-β-D-glucopyranosyluronate)-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:

benzyl bromide (100-39-0) + (2S,3S,4S,5R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-2-ethyl-3-hydroxy-4,5-dimethoxy-tetrahydro-pyran-2-carboxylic acid → methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2,3-di-O-methyl-5-C-ethyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside (229956-33-6)

Guidance literature:

With tetrabutyl-ammonium chloride; sodium hydrogencarbonate; In dichloromethane; water; at 20 ℃; for 0.75h;

DOI:10.1002/1521-3765(20011119)7:22<4821::AID-CHEM4821>3.0.CO;2-N

Reference yield:

1,2,4,6-tetra-O-acetyl-3-O-methyl-5-C-vinyl-β-D-gluco-pyranose (202648-84-8) → methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2,3-di-O-methyl-5-C-ethyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside (229956-33-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 85 percent / TMSOTf; molecular sieves / CH₂Cl₂ / 2 h / -78 - 20 °C

2: Na; MeOH / 3 h / 20 °C

3: 1.7 g / p-TsOH / acetone / 16 h / 20 °C

4: NaH / tetrahydrofuran / 1 h / 20 °C

5: 1.16 g / aq. AcOH / 3 h / 70 °C

6: 100 percent / H₂ / PtO₂ / ethyl acetate / 0.17 h / 20 °C / 1050.08 Torr

7: Bu₄NCl; aq. NaOCl; TEMPO / NaHCO₃; NaCl / CH₂Cl₂ / 0.5 h / 0 °C / KBr also present

8: 415 mg / Bu₄NCl; NaHCO₃ / CH₂Cl₂; H₂O / 0.75 h / 20 °C

With methanol; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; molecular sieve; trimethylsilyl trifluoromethanesulfonate; tetrabutyl-ammonium chloride; hydrogen; sodium; sodium hydride; sodium hydrogencarbonate; toluene-4-sulfonic acid; acetic acid; platinum(IV) oxide; sodium hydrogencarbonate; sodium chloride; In tetrahydrofuran; dichloromethane; water; ethyl acetate; acetone;

DOI:10.1002/1521-3765(20011119)7:22<4821::AID-CHEM4821>3.0.CO;2-N

Reference yield:

methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-isopropylidene-3-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside (202649-52-3) → methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2,3-di-O-methyl-5-C-ethyl-β-D-glucopyranosyluronate)-α-D-glucopyranoside (229956-33-6)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH / tetrahydrofuran / 1 h / 20 °C

2: 1.16 g / aq. AcOH / 3 h / 70 °C

3: 100 percent / H₂ / PtO₂ / ethyl acetate / 0.17 h / 20 °C / 1050.08 Torr

4: Bu₄NCl; aq. NaOCl; TEMPO / NaHCO₃; NaCl / CH₂Cl₂ / 0.5 h / 0 °C / KBr also present

5: 415 mg / Bu₄NCl; NaHCO₃ / CH₂Cl₂; H₂O / 0.75 h / 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; tetrabutyl-ammonium chloride; hydrogen; sodium hydride; sodium hydrogencarbonate; acetic acid; platinum(IV) oxide; sodium hydrogencarbonate; sodium chloride; In tetrahydrofuran; dichloromethane; water; ethyl acetate;

DOI:10.1002/1521-3765(20011119)7:22<4821::AID-CHEM4821>3.0.CO;2-N

upstream raw materials:

benzyl bromide

1,2,4,6-tetra-O-acetyl-3-O-methyl-5-C-vinyl-β-D-gluco-pyranose

methyl 2,3,6-tri-O-benzyl-4-O-(4,6-O-isopropylidene-3-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

methyl 2,3,6-tri-O-benzyl-4-O-(2,4,6-tri-O-acetyl-3-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucano-side

Downstream raw materials:

methyl (6-O-benzyl-2,3,4-tri-O-methyl-α-D-glucopyranosyl)-(1->4)-(benzyl 5-C-ethyl-2,3-di-O-methyl-β-D-glucopyranosyluronate)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

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