[methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glycopyranosyluronate]-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glycopyranosyluronate)trichloroacetimidate

Base Information

Chemical Name:[methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glycopyranosyluronate]-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glycopyranosyluronate)trichloroacetimidate
CAS No.:952721-49-2
Molecular Formula:C₅₁H₅₃Cl₃N₄O₁₂
Molecular Weight:1020.36
Hs Code.:

[methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glycopyranosyluronate]-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glycopyranosyluronate)trichloroacetimidate

Synonyms:[methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glycopyranosyluronate]-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glycopyranosyluronate)trichloroacetimidate

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Chemical Property of [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glycopyranosyluronate]-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glycopyranosyluronate)trichloroacetimidate

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Technology Process of [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glycopyranosyluronate]-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glycopyranosyluronate)trichloroacetimidate

There total 5 articles about [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glycopyranosyluronate]-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glycopyranosyluronate)trichloroacetimidate 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:

: 628280-88-6
allyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyl-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

: 952721-49-2
[methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glycopyranosyluronate]-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glycopyranosyluronate)trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

2.1: 1.86 g / NaH₂PO₄; 2-methyl-2-butene; NaO₂Cl / H₂O; 2-methyl-propan-2-ol / -10 - 20 °C

3.1: 1.41 g / Cs₂CO₃ / dimethylformamide / 16 h / 20 °C

4.1: [Ir(C₈H₁₄)(PMe₂Ph)2][PF₆]; H₂ / tetrahydrofuran / 20 °C

4.2: 83 percent / HgO; HgCl₂ / acetone; H₂O / 1 h

5.1: 88 percent / DBU / CH₂Cl₂ / 0.25 h

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; [Ir(C₈H₁₄)(PMe₂Ph)2][PF₆]; hydrogen; caesium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Swern-oxidation;
DOI:10.1002/ejoc.200300791

Reference yield:

: 628281-92-5
allyl [methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glucopyranosyluronate]-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

: 952721-49-2
[methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glycopyranosyluronate]-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glycopyranosyluronate)trichloroacetimidate

Guidance literature:: Multi-step reaction with 2 steps

1.1: [Ir(C₈H₁₄)(PMe₂Ph)2][PF₆]; H₂ / tetrahydrofuran / 20 °C

1.2: 83 percent / HgO; HgCl₂ / acetone; H₂O / 1 h

2.1: 88 percent / DBU / CH₂Cl₂ / 0.25 h

With [Ir(C₈H₁₄)(PMe₂Ph)2][PF₆]; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane;
DOI:10.1002/ejoc.200300791

Reference yield:

: 628281-08-3
allyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-β-D-glucopyranosyl-(1->4)-O-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

: 952721-49-2
[methyl 2,3-di-O-benzyl-4-O-(4-methoxybenzyl)-β-D-glycopyranosyluronate]-(1->4)-(2-azido-3,6-di-O-benzyl-2-deoxy-α,β-D-glycopyranosyluronate)trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 97 percent / PhBCl₂; Et₃SiH; 4 Angstroem molecular sieves / diethyl ether / -40 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 °C

3.1: 1.86 g / NaH₂PO₄; 2-methyl-2-butene; NaO₂Cl / H₂O; 2-methyl-propan-2-ol / -10 - 20 °C

4.1: 1.41 g / Cs₂CO₃ / dimethylformamide / 16 h / 20 °C

5.1: [Ir(C₈H₁₄)(PMe₂Ph)2][PF₆]; H₂ / tetrahydrofuran / 20 °C

5.2: 83 percent / HgO; HgCl₂ / acetone; H₂O / 1 h

6.1: 88 percent / DBU / CH₂Cl₂ / 0.25 h

With triethylsilane; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; [Ir(C₈H₁₄)(PMe₂Ph)2][PF₆]; 4 A molecular sieve; phenylborondichloride; hydrogen; caesium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: Swern-oxidation;
DOI:10.1002/ejoc.200300791