methyl 2,3,6-tri-O-benzyl-4-O-(3-O-5-C-methylene-2-O-methyl-5-C-vinyl-α-L-idopyranosyl)-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2,3,6-tri-O-benzyl-4-O-(3-O-5-C-methylene-2-O-methyl-5-C-vinyl-α-L-idopyranosyl)-α-D-glucopyranoside
CAS No.:403725-07-5
Molecular Formula:C₃₇H₄₄O₁₀
Molecular Weight:648.75
Hs Code.:

Synonyms:methyl 2,3,6-tri-O-benzyl-4-O-(3-O-5-C-methylene-2-O-methyl-5-C-vinyl-α-L-idopyranosyl)-α-D-glucopyranoside

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Chemical Property of methyl 2,3,6-tri-O-benzyl-4-O-(3-O-5-C-methylene-2-O-methyl-5-C-vinyl-α-L-idopyranosyl)-α-D-glucopyranoside

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Technology Process of methyl 2,3,6-tri-O-benzyl-4-O-(3-O-5-C-methylene-2-O-methyl-5-C-vinyl-α-L-idopyranosyl)-α-D-glucopyranoside

There total 16 articles about methyl 2,3,6-tri-O-benzyl-4-O-(3-O-5-C-methylene-2-O-methyl-5-C-vinyl-α-L-idopyranosyl)-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: 85.0%

: 403725-06-4
methyl 2,3,6-tri-O-benzyl-4-O-(3-O-acetyl-2-O-methyl-6-O-tosyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

: 403725-07-5
methyl 2,3,6-tri-O-benzyl-4-O-(3-O-5-C-methylene-2-O-methyl-5-C-vinyl-α-L-idopyranosyl)-α-D-glucopyranoside

Guidance literature:: With sodium hydroxide; In ethanol; at 70 - 80 ℃; for 2h;
DOI:10.1002/1521-3765(20011119)7:22<4821::AID-CHEM4821>3.0.CO;2-N

Reference yield:

: 19488-48-3
methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

: 403725-07-5
methyl 2,3,6-tri-O-benzyl-4-O-(3-O-5-C-methylene-2-O-methyl-5-C-vinyl-α-L-idopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: 78 percent / TMSOTf; molecular sieves / CH₂Cl₂ / 3 h / -78 - 20 °C

2: Na; MeOH / 6 h / 20 °C

3: 3.3 g / p-TsOH / acetone / 20 °C

4: 92 percent / NaH / dimethylformamide / 4 h / 20 °C

5: tBuOK / dimethylsulfoxide / 1 h / 80 °C

6: 1.83 g / HgO; aq. HgCl₂ / acetone / 1 h / 20 °C

7: pyridine / CH₂Cl₂ / 3 h / 20 °C

8: 1.0 g / aq. AcOH / 1 h / 70 °C

9: 75 percent / NEt₃ / CH₂Cl₂ / 6 h / 20 °C

10: 85 percent / NaOH / ethanol / 2 h / 70 - 80 °C

With pyridine; methanol; sodium hydroxide; molecular sieve; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; sodium; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; mercury dichloride; mercury(II) oxide; In ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;
DOI:10.1002/1521-3765(20011119)7:22<4821::AID-CHEM4821>3.0.CO;2-N

Reference yield:

: 91882-92-7
3-O-allyl-1,2-O-isopropylidene-α-D-glucofuranose

: 403725-07-5
methyl 2,3,6-tri-O-benzyl-4-O-(3-O-5-C-methylene-2-O-methyl-5-C-vinyl-α-L-idopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 15 steps

1: 95 percent / imidazole / CH₂Cl₂ / 4 h / 20 °C

2: (COCl)2; DMSO; NEt₃ / CH₂Cl₂ / 1 h / -78 °C

3: 9.9 g / tetrahydrofuran / 1 h / 0 °C

4: IR-120 H(+) resin; H₂O / 8 h / 80 °C

5: 4.3 g / pyridine / 12 h / 20 °C

6: 78 percent / TMSOTf; molecular sieves / CH₂Cl₂ / 3 h / -78 - 20 °C

7: Na; MeOH / 6 h / 20 °C

8: 3.3 g / p-TsOH / acetone / 20 °C

9: 92 percent / NaH / dimethylformamide / 4 h / 20 °C

10: tBuOK / dimethylsulfoxide / 1 h / 80 °C

11: 1.83 g / HgO; aq. HgCl₂ / acetone / 1 h / 20 °C

12: pyridine / CH₂Cl₂ / 3 h / 20 °C

13: 1.0 g / aq. AcOH / 1 h / 70 °C

14: 75 percent / NEt₃ / CH₂Cl₂ / 6 h / 20 °C

15: 85 percent / NaOH / ethanol / 2 h / 70 - 80 °C

With pyridine; 1H-imidazole; methanol; sodium hydroxide; molecular sieve; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; IR-120 H(+) resin; potassium tert-butylate; water; sodium; sodium hydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; 2: Swern oxidation / 3: Grignard reaction;
DOI:10.1002/1521-3765(20011119)7:22<4821::AID-CHEM4821>3.0.CO;2-N