allyl (β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-6-O-tert-butyldiphenylsilyl)]-β-D-glucopyranoside

Base Information

Chemical Name:allyl (β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-6-O-tert-butyldiphenylsilyl)]-β-D-glucopyranoside
CAS No.:200003-75-4
Molecular Formula:C₆₅H₇₈O₁₅Si
Molecular Weight:1127.41
Hs Code.:

Synonyms:allyl (β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-6-O-tert-butyldiphenylsilyl)]-β-D-glucopyranoside

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Chemical Property of allyl (β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-6-O-tert-butyldiphenylsilyl)]-β-D-glucopyranoside

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Technology Process of allyl (β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-6-O-tert-butyldiphenylsilyl)]-β-D-glucopyranoside

There total 12 articles about allyl (β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-6-O-tert-butyldiphenylsilyl)]-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: 92.0%

: 200003-56-1
allyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-6-O-tert-butyldiphenylsilyl)]-β-D-glucopyranoside

: 200003-75-4
allyl (β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-6-O-tert-butyldiphenylsilyl)]-β-D-glucopyranoside

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 12h;
DOI:10.1016/S0040-4020(97)01024-7

Reference yield:

: 13322-90-2
3,4,6-tri-O-benzoyl-D-glucal

: 200003-75-4
allyl (β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-6-O-tert-butyldiphenylsilyl)]-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1: 99 percent / 4-methylmorpholine N-oxide / osmium tetraoxide / acetone; H₂O; 2-methyl-propan-2-ol / 120 h

2: 88 percent / thionyl diimidazole / tetrahydrofuran / 0.33 h / -20 °C

3: 76 percent / 3 Angstroem molecular sieves / ytterbium(III) triflate / toluene / 12 h / 100 °C

4: 95 percent / trifluoromethane sulfonic acid / CH₂Cl₂; cyclohexane / 4 h / 20 °C

5: 91 percent / sodium methoxide / methanol / 12 h

6: 77 percent / p-toluenesulfonic acid / dimethylformamide / 17 h / 50 °C / reduced pressure

7: 76 percent / dibutyltin dichloride; 2,6-di-tert-butyl-4-methylpyridine; silver triflate / toluene / 0.25 h / 20 °C

8: 82 percent / p-toluenesulfonic acid monohydrate / CHCl₃; methanol / 24 h / 20 °C

9: 95 percent / triethylamine; N,N-dimethylaminopyridine / CH₂Cl₂ / 8 h / 20 °C

10: 89 percent / triflic acid / diethyl ether / 1 h / 0 °C

11: 92 percent / potassium carbonate / methanol / 12 h / 20 °C

With dmap; 2,6-di-tert-butyl-4-methylpyridine; trifluorormethanesulfonic acid; 3 A molecular sieve; thionyl diimidazole; dibutyltin chloride; sodium methylate; silver trifluoromethanesulfonate; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; osmium(VIII) oxide; ytterbium(III) triflate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; cyclohexane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 1: Oxidation / 2: Cyclization / 3: glycosylation / 4: Etherification / 5: methanolysis / 6: Cyclization / 7: glycosylation / 8: solvolysis / 9: silylation / 10: glycosylation / 11: Deacetylation;
DOI:10.1016/S0040-4020(97)01024-7

Reference yield:

: 3,4,6-tri-O-benzoyl-α,β-D-glucopyranose

: 200003-75-4
allyl (β-D-galactopyranosyl)1->4[(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)1->3(2-O-benzyl-6-O-tert-butyldiphenylsilyl)]-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1: 88 percent / thionyl diimidazole / tetrahydrofuran / 0.33 h / -20 °C

2: 76 percent / 3 Angstroem molecular sieves / ytterbium(III) triflate / toluene / 12 h / 100 °C

3: 95 percent / trifluoromethane sulfonic acid / CH₂Cl₂; cyclohexane / 4 h / 20 °C

4: 91 percent / sodium methoxide / methanol / 12 h

5: 77 percent / p-toluenesulfonic acid / dimethylformamide / 17 h / 50 °C / reduced pressure

6: 76 percent / dibutyltin dichloride; 2,6-di-tert-butyl-4-methylpyridine; silver triflate / toluene / 0.25 h / 20 °C

7: 82 percent / p-toluenesulfonic acid monohydrate / CHCl₃; methanol / 24 h / 20 °C

8: 95 percent / triethylamine; N,N-dimethylaminopyridine / CH₂Cl₂ / 8 h / 20 °C

9: 89 percent / triflic acid / diethyl ether / 1 h / 0 °C

10: 92 percent / potassium carbonate / methanol / 12 h / 20 °C

With dmap; 2,6-di-tert-butyl-4-methylpyridine; trifluorormethanesulfonic acid; 3 A molecular sieve; thionyl diimidazole; dibutyltin chloride; sodium methylate; silver trifluoromethanesulfonate; potassium carbonate; toluene-4-sulfonic acid; triethylamine; ytterbium(III) triflate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; chloroform; cyclohexane; N,N-dimethyl-formamide; toluene; 1: Cyclization / 2: glycosylation / 3: Etherification / 4: methanolysis / 5: Cyclization / 6: glycosylation / 7: solvolysis / 8: silylation / 9: glycosylation / 10: Deacetylation;
DOI:10.1016/S0040-4020(97)01024-7