methyl 4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-D-glucopyranoside

Base Information

Chemical Name:methyl 4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-D-glucopyranoside
CAS No.:1415974-52-5
Molecular Formula:C₆₁H₆₅N₃O₁₁Si
Molecular Weight:1044.29
Hs Code.:

methyl 4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-D-glucopyranoside

Synonyms:methyl 4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-D-glucopyranoside

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Chemical Property of methyl 4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-D-glucopyranoside

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Technology Process of methyl 4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-D-glucopyranoside

There total 8 articles about methyl 4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-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: 93.0%

: 1415973-56-6
methyl 6-O-acetyl-4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-D-glucopyranoside

: 1415974-52-5
methyl 4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-D-glucopyranoside

Guidance literature:: With magnesium methanolate; In methanol; dichloromethane; for 2h;
DOI:10.1021/ja3090065

Reference yield:

: 918948-16-0
p-methylphenyl 2-O-benzoyl-3-O-benzyl-1-thio-β-D-glucopyranoside

: 1415974-52-5
methyl 4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: triethylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere

2: trimethylsilyl trifluoromethanesulfonate; N-iodo-succinimide / dichloromethane / 2 h / -78 - -20 °C / Inert atmosphere; Molecular sieve

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / -78 - -20 °C / Inert atmosphere; Molecular sieve

4: magnesium methanolate / methanol; dichloromethane / 2 h

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; magnesium methanolate; triethylamine; In methanol; dichloromethane;
DOI:10.1021/ja3090065

Reference yield:

: 942043-17-6
4-methylphenyl 2,3,4,6-tetrakis-O-trimethylsilyl-1-thio-β-D-glucopyranoside

: 1415974-52-5
methyl 4-O-[2-azido-4-O-benzyl-6-O-(tert-butyldiphenylsilyl)-2-deoxy-3-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 °C / Inert atmosphere; Molecular sieve

2: trimethylsilyl trifluoromethanesulfonate; triethylsilane / dichloromethane / 4 h / -78 °C / Inert atmosphere; Molecular sieve

3: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 18 h / 0 °C / Inert atmosphere; Molecular sieve

4: trifluoroacetic acid; water / dichloromethane / 3 h / 20 °C / Inert atmosphere; Molecular sieve

5: triethylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere

6: trimethylsilyl trifluoromethanesulfonate; N-iodo-succinimide / dichloromethane / 2 h / -78 - -20 °C / Inert atmosphere; Molecular sieve

7: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 3 h / -78 - -20 °C / Inert atmosphere; Molecular sieve

8: magnesium methanolate / methanol; dichloromethane / 2 h

With triethylsilane; N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; water; magnesium methanolate; triethylamine; trifluoroacetic acid; In methanol; dichloromethane;
DOI:10.1021/ja3090065