methyl O-(2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-(1<>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<>3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

Base Information

Chemical Name:methyl O-(2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside
CAS No.:160529-60-2
Molecular Formula:C₅₄H₆₁NO₁₄
Molecular Weight:948.077
Hs Code.:

methyl O-(2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

Synonyms:methyl O-(2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

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Chemical Property of methyl O-(2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

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Technology Process of methyl O-(2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

There total 11 articles about methyl O-(2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside 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: 79.0%

: 160529-53-3
methyl O-(2-azido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzyl-α-L-rhamnopyranoside

: 160529-60-2
methyl O-(2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

Guidance literature:: With sodium tetrahydroborate; boric acid; nickel dichloride; In 1,2-dimethoxyethane; ethanol; at 25 ℃;
DOI:10.1016/0008-6215(94)80035-9

Reference yield:

: 69850-47-1
(2R,3R,4R,5R,6S)-3,5-Bis-benzyloxy-2-methoxy-6-methyl-tetrahydro-pyran-4-ol

: 160529-60-2
methyl O-(2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 21 percent / MeSiOTf, 4A molecular sieves / CH₂Cl₂ / 5 h / 25 °C

2: 86 percent / HBF₄ / methanol; diethyl ether / 24 h / 25 °C

3: 53 percent / 2,6-di-tert-butyl-4-methylpyridine, 4A molecular sieves, AgOTf / CH₂Cl₂ / 1 h

4: 92 percent / thiourea / CH₂Cl₂; methanol / 1 h / 25 °C

5: 79 percent / NiCl₂*6H₂O, H₃BO₃, NaBH₄ / 1,2-dimethoxy-ethane; ethanol / 25 °C

With sodium tetrahydroborate; tetrafluoroboric acid; 2,6-di-tert-butyl-4-methylpyridine; MeSiOTf; 4 A molecular sieve; silver trifluoromethanesulfonate; boric acid; thiourea; nickel dichloride; In methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane;
DOI:10.1016/0008-6215(94)80035-9

Reference yield:

: 90164-72-0
methyl 2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranoside

: 160529-60-2
methyl O-(2-amino-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl)-(1<*>3)-O-(2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl)-(1<*>3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / pyridine / 2 h / 25 °C

2: 30 percent / conc. H₂SO₄ / 0.5 h

3: 21 percent / MeSiOTf, 4A molecular sieves / CH₂Cl₂ / 5 h / 25 °C

4: 86 percent / HBF₄ / methanol; diethyl ether / 24 h / 25 °C

5: 53 percent / 2,6-di-tert-butyl-4-methylpyridine, 4A molecular sieves, AgOTf / CH₂Cl₂ / 1 h

6: 92 percent / thiourea / CH₂Cl₂; methanol / 1 h / 25 °C

7: 79 percent / NiCl₂*6H₂O, H₃BO₃, NaBH₄ / 1,2-dimethoxy-ethane; ethanol / 25 °C

With pyridine; sodium tetrahydroborate; tetrafluoroboric acid; 2,6-di-tert-butyl-4-methylpyridine; MeSiOTf; 4 A molecular sieve; sulfuric acid; silver trifluoromethanesulfonate; boric acid; thiourea; nickel dichloride; In methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane;
DOI:10.1016/0008-6215(94)80035-9