allyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:allyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
CAS No.:158420-83-8
Molecular Formula:C₃₃H₃₂ClNO₈
Molecular Weight:606.072
Hs Code.:

Synonyms:allyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-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 allyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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Technology Process of allyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 7 articles about allyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-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: 88.0%

: 89067-88-9
allyl-3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

: 79-04-9
chloroacetyl chloride

: 158420-83-8
allyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: In pyridine; at 0 ℃; for 0.5h;
DOI:10.1016/S0040-4039(00)61560-5

Reference yield:

: 10022-13-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

: 158420-83-8
allyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 81 percent / trimethylsilyl triflate / CH₂Cl₂

2: 90 percent / conc. HCl / acetone / 70 °C

3: 95 percent / TsOH / dimethylformamide / 50 °C

4: 48 percent / CF₃SO₃H / CH₂Cl₂ / 2 h / 0 °C / pH 3

5: 93 percent / aq. AcOH / 1.5 h / 70 °C

6: 1.) (Bu₃Sn)2O, 2.) Bu₄NI / 1.) toluene, reflux, 4 h, 2.) 110 deg C, 5 h

7: 88 percent / pyridine / 1,2-dichloro-ethane / 0.5 h / 10 °C

With pyridine; hydrogenchloride; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; acetic acid; bis(tri-n-butyltin)oxide; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;

Reference yield:

: 72333-26-7
allyl 3,4,6-tri-O-acetyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

: 158420-83-8
allyl 3,6-di-O-benzyl-4-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 90 percent / conc. HCl / acetone / 70 °C

2: 95 percent / TsOH / dimethylformamide / 50 °C

3: 48 percent / CF₃SO₃H / CH₂Cl₂ / 2 h / 0 °C / pH 3

4: 93 percent / aq. AcOH / 1.5 h / 70 °C

5: 1.) (Bu₃Sn)2O, 2.) Bu₄NI / 1.) toluene, reflux, 4 h, 2.) 110 deg C, 5 h

6: 88 percent / pyridine / 1,2-dichloro-ethane / 0.5 h / 10 °C

With pyridine; hydrogenchloride; trifluorormethanesulfonic acid; tetra-(n-butyl)ammonium iodide; toluene-4-sulfonic acid; acetic acid; bis(tri-n-butyltin)oxide; In dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;