benzyl O-(3',4',6'-tri-O-benzyl-α-D-galactopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-2',3'-succinate

Base Information

Chemical Name:benzyl O-(3',4',6'-tri-O-benzyl-α-D-galactopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-2',3'-succinate
CAS No.:259871-07-3
Molecular Formula:C₅₈H₅₈O₁₄
Molecular Weight:979.09
Hs Code.:

Synonyms:benzyl O-(3',4',6'-tri-O-benzyl-α-D-galactopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-2',3'-succinate

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Chemical Property of benzyl O-(3',4',6'-tri-O-benzyl-α-D-galactopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-2',3'-succinate

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Technology Process of benzyl O-(3',4',6'-tri-O-benzyl-α-D-galactopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-2',3'-succinate

There total 6 articles about benzyl O-(3',4',6'-tri-O-benzyl-α-D-galactopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-2',3'-succinate 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: 51.0%

: 259871-02-8
phenyl 3,4,6-tri-O-benzyl-2-O-(2-O-benzoyl-1,4-di-O-benzyl-α-D-glucopyranos-3-yloxycarbonylpropanoyl)-1-thio-β-D-galactopyranoside

: 259871-07-3
benzyl O-(3',4',6'-tri-O-benzyl-α-D-galactopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-2',3'-succinate

Guidance literature:: With N-iodo-succinimide; molecular sieve; trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at -30 ℃; for 0.166667h;
DOI:10.1080/07328309908544056

Reference yield:

: 68779-52-2
1,2-O-(1-methoxyethylidene)-3,4,6-tri-O-benzyl-α-D-galactopyranose

: 259871-07-3
benzyl O-(3',4',6'-tri-O-benzyl-α-D-galactopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-2',3'-succinate

Guidance literature:: Multi-step reaction with 6 steps

1: 80 percent / HgBr₂ / acetonitrile / 24 h / 20 °C

2: 72 percent / NaOMe / methanol; toluene / 2.5 h / 75 °C

3: 97 percent / DMAP / pyridine / 22.5 h / 100 °C

4: 72 percent / DCC; DMAP / CH₂Cl₂ / 20 h / 20 °C

5: 74 percent / NaCNBH₃; HCl; molecular sieves / diethyl ether; tetrahydrofuran / 0 °C

6: 51 percent / TMSOTf; NIS; molecular sieves / acetonitrile / 0.17 h / -30 °C

With hydrogenchloride; dmap; N-iodo-succinimide; molecular sieve; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium cyanoborohydride; dicyclohexyl-carbodiimide; mercury dibromide; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; toluene; acetonitrile; 1: Ring cleavage / 2: Deacetylation / 3: Esterification / 4: Condensation / 5: Reduction / 6: Cyclization;
DOI:10.1080/07328309908544056

Reference yield:

: 183875-28-7
phenyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside

: 259871-07-3
benzyl O-(3',4',6'-tri-O-benzyl-α-D-galactopyranosyl)-(1->4)-2-O-benzoyl-6-O-benzyl-α-D-glucopyranoside-2',3'-succinate

Guidance literature:: Multi-step reaction with 5 steps

1: 72 percent / NaOMe / methanol; toluene / 2.5 h / 75 °C

2: 97 percent / DMAP / pyridine / 22.5 h / 100 °C

3: 72 percent / DCC; DMAP / CH₂Cl₂ / 20 h / 20 °C

4: 74 percent / NaCNBH₃; HCl; molecular sieves / diethyl ether; tetrahydrofuran / 0 °C

5: 51 percent / TMSOTf; NIS; molecular sieves / acetonitrile / 0.17 h / -30 °C

With hydrogenchloride; dmap; N-iodo-succinimide; molecular sieve; trimethylsilyl trifluoromethanesulfonate; sodium methylate; sodium cyanoborohydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; toluene; acetonitrile; 1: Deacetylation / 2: Esterification / 3: Condensation / 4: Reduction / 5: Cyclization;
DOI:10.1080/07328309908544056