2-bromoethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Base Information

Chemical Name:2-bromoethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside
CAS No.:89983-49-3
Molecular Formula:C₄₄H₄₈BrNO₁₆
Molecular Weight:926.766
Hs Code.:

Synonyms:2-bromoethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

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Chemical Property of 2-bromoethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

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Technology Process of 2-bromoethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

There total 9 articles about 2-bromoethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-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: 75.0%

: 89983-48-2
2-bromoethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

: 3068-32-4
1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

: 89983-49-3
2-bromoethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Guidance literature:: With silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane; -70 deg C to room temperature;
DOI:10.1016/0008-6215(84)85159-9

Reference yield:

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

: 89983-49-3
2-bromoethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: BF₃ etherate

2: 73 percent / aqu. HCl / acetone / 3.5 h / 70 °C

3: 86 percent / TsOH_.H₂O / acetonitrile / 1 h / Ambient temperature

4: 69 percent / CF₃SO₃H / cyclohexane; CH₂Cl₂ / 2.7 h / Ambient temperature

5: 93 percent / HCl, Na-cyanoborohydride / diethyl ether; tetrahydrofuran

6: 75 percent / Ag-triflate, tetramethylurea / CH₂Cl₂ / -70 deg C to room temperature

With hydrogenchloride; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; silver trifluoromethanesulfonate; sodium cyanoborohydride; toluene-4-sulfonic acid; tetramethylurea; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; acetone; acetonitrile;
DOI:10.1016/0008-6215(84)85159-9

Reference yield:

: 85-44-9
phthalic anhydride

: 89983-49-3
2-bromoethyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) Et₃N, 2.) pyridine / 1.) MeOH, water, 1 h, 50 deg C; 2.) 1 h, 100 deg C

2: BF₃ etherate

3: 73 percent / aqu. HCl / acetone / 3.5 h / 70 °C

4: 86 percent / TsOH_.H₂O / acetonitrile / 1 h / Ambient temperature

5: 69 percent / CF₃SO₃H / cyclohexane; CH₂Cl₂ / 2.7 h / Ambient temperature

6: 93 percent / HCl, Na-cyanoborohydride / diethyl ether; tetrahydrofuran

7: 75 percent / Ag-triflate, tetramethylurea / CH₂Cl₂ / -70 deg C to room temperature

With pyridine; hydrogenchloride; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; silver trifluoromethanesulfonate; sodium cyanoborohydride; toluene-4-sulfonic acid; triethylamine; tetramethylurea; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; acetone; acetonitrile;
DOI:10.1016/0008-6215(84)85159-9