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

Base Information

Chemical Name:methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2-O-methyl-3-O-5-C-methylene-α-L-idopyranosyluronate)-α-D-glucopyranoside
CAS No.:403725-08-6
Molecular Formula:C₄₃H₄₈O₁₂
Molecular Weight:756.847
Hs Code.:

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

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

Chemical Property:

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

There total 19 articles about methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2-O-methyl-3-O-5-C-methylene-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:

: 100-39-0
benzyl bromide

: (1R,3R,4R,5S,8S)-3-((2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-8-hydroxy-4-methoxy-2,6-dioxa-bicyclo[3.2.1]octane-1-carboxylic acid

: 403725-08-6
methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2-O-methyl-3-O-5-C-methylene-α-L-idopyranosyluronate)-α-D-glucopyranoside

Guidance literature:: With tetra-(n-butyl)ammonium iodide; potassium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 5h;
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

: 403725-08-6
methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2-O-methyl-3-O-5-C-methylene-α-L-idopyranosyluronate)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 13 steps

1.1: 78 percent / TMSOTf; molecular sieves / CH₂Cl₂ / 3 h / -78 - 20 °C

2.1: Na; MeOH / 6 h / 20 °C

3.1: 3.3 g / p-TsOH / acetone / 20 °C

4.1: 92 percent / NaH / dimethylformamide / 4 h / 20 °C

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

6.1: 1.83 g / HgO; aq. HgCl₂ / acetone / 1 h / 20 °C

7.1: pyridine / CH₂Cl₂ / 3 h / 20 °C

8.1: 1.0 g / aq. AcOH / 1 h / 70 °C

9.1: 75 percent / NEt₃ / CH₂Cl₂ / 6 h / 20 °C

10.1: 85 percent / NaOH / ethanol / 2 h / 70 - 80 °C

11.1: O₃ / CH₂Cl₂ / -78 °C

11.2: Me₂S / CH₂Cl₂ / 1 h / 20 °C

12.1: aq. NaH₂PO₄; 2-methyl-2-butene; NaClO₂ / 2-methyl-propan-2-ol / 5 h / 20 °C

13.1: 0.17 g / KHCO₃; Bu₄NI / dimethylformamide / 5 h / 20 °C

With pyridine; methanol; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; molecular sieve; 2-methyl-but-2-ene; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; triethylamine; mercury dichloride; mercury(II) oxide; In ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;
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

: 403725-08-6
methyl 2,3,6-tri-O-benzyl-4-O-(benzyl 2-O-methyl-3-O-5-C-methylene-α-L-idopyranosyluronate)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 18 steps

1.1: 95 percent / imidazole / CH₂Cl₂ / 4 h / 20 °C

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

3.1: 9.9 g / tetrahydrofuran / 1 h / 0 °C

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

5.1: 4.3 g / pyridine / 12 h / 20 °C

6.1: 78 percent / TMSOTf; molecular sieves / CH₂Cl₂ / 3 h / -78 - 20 °C

7.1: Na; MeOH / 6 h / 20 °C

8.1: 3.3 g / p-TsOH / acetone / 20 °C

9.1: 92 percent / NaH / dimethylformamide / 4 h / 20 °C

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

11.1: 1.83 g / HgO; aq. HgCl₂ / acetone / 1 h / 20 °C

12.1: pyridine / CH₂Cl₂ / 3 h / 20 °C

13.1: 1.0 g / aq. AcOH / 1 h / 70 °C

14.1: 75 percent / NEt₃ / CH₂Cl₂ / 6 h / 20 °C

15.1: 85 percent / NaOH / ethanol / 2 h / 70 - 80 °C

16.1: O₃ / CH₂Cl₂ / -78 °C

16.2: Me₂S / CH₂Cl₂ / 1 h / 20 °C

17.1: aq. NaH₂PO₄; 2-methyl-2-butene; NaClO₂ / 2-methyl-propan-2-ol / 5 h / 20 °C

18.1: 0.17 g / KHCO₃; Bu₄NI / dimethylformamide / 5 h / 20 °C

With pyridine; 1H-imidazole; methanol; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; molecular sieve; 2-methyl-but-2-ene; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; IR-120 H(+) resin; potassium tert-butylate; water; sodium; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; dimethyl sulfoxide; triethylamine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 2.1: Swern oxidation / 3.1: Grignard reaction;
DOI:10.1002/1521-3765(20011119)7:22<4821::AID-CHEM4821>3.0.CO;2-N