methyl 2,4-di-O-acetyl-6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-glycero-α-D-manno-heptopyranoside

Base Information

Chemical Name:methyl 2,4-di-O-acetyl-6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-glycero-α-D-manno-heptopyranoside
CAS No.:131289-52-6
Molecular Formula:C₅₉H₇₂O₁₅Si
Molecular Weight:1049.3
Hs Code.:

methyl 2,4-di-O-acetyl-6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-glycero-α-D-manno-heptopyranoside

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Chemical Property of methyl 2,4-di-O-acetyl-6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-glycero-α-D-manno-heptopyranoside

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Technology Process of methyl 2,4-di-O-acetyl-6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-glycero-α-D-manno-heptopyranoside

There total 8 articles about methyl 2,4-di-O-acetyl-6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-glycero-α-D-manno-heptopyranoside 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: 70.0%

: 104992-64-5,162061-34-9
methyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside

: methyl 2,4-di-O-acetyl-6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-L-glycero-α-D-manno-heptopyranoside

: 131289-53-7
methyl 2,4-di-O-acetyl-6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-3-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-L-glycero-α-D-manno-heptopyranoside

: 131289-52-6
methyl 2,4-di-O-acetyl-6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: With 4 A molecular sieve; triethylamine; methyl trifluoromethanesulfonate; In diethyl ether; for 0.5h;
DOI:10.1016/0008-6215(90)80133-N

Reference yield:

: 40653-15-4
methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside

: 131289-52-6
methyl 2,4-di-O-acetyl-6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 9 steps

1: 1) magnesium, dibromoethane / 1) THF, reflux, 2) 2 h, 0 deg C

2: 3.7 g / 30percent H₂O₂, NaHCO₃ / methanol; tetrahydrofuran / 15 h / Heating

3: pyridine / 0 deg C to r. t., overnight

4: 0.41 g / pyridine, 4-dimethylaminopyridine / 0.5 h

5: 82 percent / H₂ / 10percent Pd-C / ethyl acetate / 24 h / 3000.2 Torr

6: p-toluenesulfonic acid / acetonitrile / 0.5 h / Ambient temperature

7: pyridine, 4-dimethylaminopyridine / acetonitrile / 1 h

8: 0.58 g / 90percent aq. trifluoroacetic acid / acetonitrile / 0.5 h

9: halide-assisted

With pyridine; dmap; 1,1-Dibromoethane; hydrogen; dihydrogen peroxide; sodium hydrogencarbonate; toluene-4-sulfonic acid; magnesium; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; acetonitrile;
DOI:10.1016/0008-6215(90)80133-N

Reference yield:

: 131289-43-5
methyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-L-glycero-α-D-manno-heptopyranoside

: 131289-52-6
methyl 2,4-di-O-acetyl-6-O-benzoyl-7-O-(tert-butyldimethylsilyl)-3-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-glycero-α-D-manno-heptopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / H₂ / 10percent Pd-C / ethyl acetate / 24 h / 3000.2 Torr

2: p-toluenesulfonic acid / acetonitrile / 0.5 h / Ambient temperature

3: pyridine, 4-dimethylaminopyridine / acetonitrile / 1 h

4: 0.58 g / 90percent aq. trifluoroacetic acid / acetonitrile / 0.5 h

5: halide-assisted

With pyridine; dmap; hydrogen; toluene-4-sulfonic acid; trifluoroacetic acid; palladium on activated charcoal; In ethyl acetate; acetonitrile;
DOI:10.1016/0008-6215(90)80133-N