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

Base Information

Chemical Name:methyl 2,3,6-tri-O-benzyl-4-O-(3-O-allyl-4,6-O-isopropylidene-2-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside
CAS No.:403725-03-1
Molecular Formula:C₄₃H₅₄O₁₁
Molecular Weight:746.895
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 10 articles about methyl 2,3,6-tri-O-benzyl-4-O-(3-O-allyl-4,6-O-isopropylidene-2-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-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: 92.0%

: 403725-02-0
methyl 2,3,6-tri-O-benzyl-4-O-(3-O-allyl-4,6-O-isopropylidene-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

: 74-88-4
methyl iodide

: 403725-03-1
methyl 2,3,6-tri-O-benzyl-4-O-(3-O-allyl-4,6-O-isopropylidene-2-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 4h;
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

: 403725-03-1
methyl 2,3,6-tri-O-benzyl-4-O-(3-O-allyl-4,6-O-isopropylidene-2-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 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

With methanol; molecular sieve; trimethylsilyl trifluoromethanesulfonate; sodium; sodium hydride; toluene-4-sulfonic acid; In dichloromethane; 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

: 403725-03-1
methyl 2,3,6-tri-O-benzyl-4-O-(3-O-allyl-4,6-O-isopropylidene-2-O-methyl-5-C-vinyl-β-D-glucopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 9 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

With pyridine; 1H-imidazole; methanol; molecular sieve; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; IR-120 H(+) resin; water; sodium; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 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