methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2,3-di-O-methyl-5-C-methoxymethyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2,3-di-O-methyl-5-C-methoxymethyl-α-L-idopyranosyluronate)-α-D-glucopyranoside
• CAS No.: 403725-22-4
• Molecular Formula: C₄₅H₅₄O₁₃
• Molecular Weight: 802.916

Synonyms:methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2,3-di-O-methyl-5-C-methoxymethyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Chemical Property of methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2,3-di-O-methyl-5-C-methoxymethyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2,3-di-O-methyl-5-C-methoxymethyl-α-L-idopyranosyluronate)-α-D-glucopyranoside

There total 10 articles about methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2,3-di-O-methyl-5-C-methoxymethyl-α-L-idopyranosyluronate)-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) + (2R,3S,4S,5R,6R)-6-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-3-hydroxy-4,5-dimethoxy-2-methoxymethyl-tetrahydro-pyran-2-carboxylic acid → methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2,3-di-O-methyl-5-C-methoxymethyl-α-L-idopyranosyluronate)-α-D-glucopyranoside (403725-22-4)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 6h;

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-(2,4,6-tri-O-acetyl-3-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucano-side (202648-85-9) → methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2,3-di-O-methyl-5-C-methoxymethyl-α-L-idopyranosyluronate)-α-D-glucopyranoside (403725-22-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: Na; MeOH / 3 h / 20 °C

2.1: 1.7 g / p-TsOH / acetone / 16 h / 20 °C

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

4.1: 1.16 g / aq. AcOH / 3 h / 70 °C

5.1: Bu₂SnO / toluene / 3 h / Heating

5.2: 65 percent / dimethylformamide / 6 h / 50 °C

6.1: O₃ / CH₂Cl₂ / -78 °C

6.2: Me₂S / CH₂Cl₂

7.1: 2-methyl-2-butene; aq. NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol / 16 h / 20 °C

8.1: 0.534 g / Bu₄NI; KHCO₃ / dimethylformamide / 6 h / 20 °C

With methanol; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; potassium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;

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-methoxymethyl-α-L-idopyranosyluronate)-α-D-glucopyranoside (403725-22-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 85 percent / TMSOTf; molecular sieves / CH₂Cl₂ / 2 h / -78 - 20 °C

2.1: Na; MeOH / 3 h / 20 °C

3.1: 1.7 g / p-TsOH / acetone / 16 h / 20 °C

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

5.1: 1.16 g / aq. AcOH / 3 h / 70 °C

6.1: Bu₂SnO / toluene / 3 h / Heating

6.2: 65 percent / dimethylformamide / 6 h / 50 °C

7.1: O₃ / CH₂Cl₂ / -78 °C

7.2: Me₂S / CH₂Cl₂

8.1: 2-methyl-2-butene; aq. NaH₂PO₄; NaClO₂ / 2-methyl-propan-2-ol / 16 h / 20 °C

9.1: 0.534 g / Bu₄NI; KHCO₃ / dimethylformamide / 6 h / 20 °C

With methanol; sodium chlorite; sodium dihydrogenphosphate; molecular sieve; 2-methyl-but-2-ene; trimethylsilyl trifluoromethanesulfonate; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; potassium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;

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

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