allyl (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside

Base Information

Chemical Name:allyl (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside
CAS No.:727380-38-3
Molecular Formula:C₄₄H₄₉N₃O₁₁
Molecular Weight:795.887
Hs Code.:

Synonyms:allyl (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of allyl (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside

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Technology Process of allyl (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside

There total 5 articles about allyl (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside 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: 96.0%

: 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

: 727380-38-3
allyl (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.25h;
DOI:10.1002/ejoc.200300791

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

: 727380-38-3
allyl (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside

Guidance literature:: Multi-step reaction with 4 steps

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

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

3: 1.41 g / Cs₂CO₃ / dimethylformamide / 16 h / 20 °C

4: 96 percent / CF₃COOH / CH₂Cl₂ / 0.25 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; caesium carbonate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Swern-oxidation;
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

: 727380-38-3
allyl (methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-α-D-glycopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / PhBCl₂; Et₃SiH; 4 Angstroem molecular sieves / diethyl ether / -40 °C

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

3: 1.86 g / NaH₂PO₄; 2-methyl-2-butene; NaO₂Cl / H₂O; 2-methyl-propan-2-ol / -10 - 20 °C

4: 1.41 g / Cs₂CO₃ / dimethylformamide / 16 h / 20 °C

5: 96 percent / CF₃COOH / CH₂Cl₂ / 0.25 h / 20 °C

With triethylsilane; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; phenylborondichloride; caesium carbonate; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2: Swern-oxidation;
DOI:10.1002/ejoc.200300791