methyl (phenyl 4-O-[2,3,4-tri-O-benzyl-6-O-{9-fluorenylmethoxycarbonyl}-α-D-glucopyranosyl]-2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)

Base Information

Chemical Name:methyl (phenyl 4-O-[2,3,4-tri-O-benzyl-6-O-{9-fluorenylmethoxycarbonyl}-α-D-glucopyranosyl]-2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)
CAS No.:1319717-46-8
Molecular Formula:C₅₅H₅₂N₆O₁₁S
Molecular Weight:1005.12
Hs Code.:

methyl (phenyl 4-O-[2,3,4-tri-O-benzyl-6-O-{9-fluorenylmethoxycarbonyl}-α-D-glucopyranosyl]-2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)

Synonyms:methyl (phenyl 4-O-[2,3,4-tri-O-benzyl-6-O-{9-fluorenylmethoxycarbonyl}-α-D-glucopyranosyl]-2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)

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Chemical Property of methyl (phenyl 4-O-[2,3,4-tri-O-benzyl-6-O-{9-fluorenylmethoxycarbonyl}-α-D-glucopyranosyl]-2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)

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Technology Process of methyl (phenyl 4-O-[2,3,4-tri-O-benzyl-6-O-{9-fluorenylmethoxycarbonyl}-α-D-glucopyranosyl]-2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)

There total 6 articles about methyl (phenyl 4-O-[2,3,4-tri-O-benzyl-6-O-{9-fluorenylmethoxycarbonyl}-α-D-glucopyranosyl]-2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate) 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%

: 1319717-07-1
methyl (phenyl 2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)

: 1384160-41-1
C₅₀H₄₄F₃NO₈

: 1319717-46-8
methyl (phenyl 4-O-[2,3,4-tri-O-benzyl-6-O-{9-fluorenylmethoxycarbonyl}-α-D-glucopyranosyl]-2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)

Guidance literature:: With trifluorormethanesulfonic acid; In diethyl ether; toluene; at -40 - -10 ℃; Molecular sieve;
DOI:10.1021/jo201179p

Reference yield:

: 1319717-03-7
phenyl 2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranoside

: 1319717-46-8
methyl (phenyl 4-O-[2,3,4-tri-O-benzyl-6-O-{9-fluorenylmethoxycarbonyl}-α-D-glucopyranosyl]-2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)

Guidance literature:: Multi-step reaction with 3 steps

1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; ethyl acetate / 1 h / 0 - 20 °C

2: potassium carbonate / N,N-dimethyl-formamide / 20 °C

3: trifluorormethanesulfonic acid / diethyl ether; toluene / -40 - -10 °C / Molecular sieve

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trifluorormethanesulfonic acid; [bis(acetoxy)iodo]benzene; potassium carbonate; In diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo201179p

Reference yield:

: 1319717-00-4
phenyl 4,6-di-O-acetyl-2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranoside

: 1319717-46-8
methyl (phenyl 4-O-[2,3,4-tri-O-benzyl-6-O-{9-fluorenylmethoxycarbonyl}-α-D-glucopyranosyl]-2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium methylate / methanol / 1.5 h

1.2: Amberlite-H⁺

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; ethyl acetate / 1 h / 0 - 20 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C

4.1: trifluorormethanesulfonic acid / diethyl ether; toluene / -40 - -10 °C / Molecular sieve

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trifluorormethanesulfonic acid; [bis(acetoxy)iodo]benzene; sodium methylate; potassium carbonate; In methanol; diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo201179p