methyl (2,3,4-tri-O-benzyl-α-L-mannopyranosyl)-(1->3)-(4-O-benzyl-2-chloro-2-deoxy-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-(N-fluorenylmethoxycarbonyl-β-alanyl)-amido-β-D-glucopyranoside

Base Information

Chemical Name:methyl (2,3,4-tri-O-benzyl-α-L-mannopyranosyl)-(1->3)-(4-O-benzyl-2-chloro-2-deoxy-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-(N-fluorenylmethoxycarbonyl-β-alanyl)-amido-β-D-glucopyranoside
CAS No.:864815-52-1
Molecular Formula:C₇₂H₇₇ClN₂O₁₆
Molecular Weight:1261.86
Hs Code.:

methyl (2,3,4-tri-O-benzyl-α-L-mannopyranosyl)-(1->3)-(4-O-benzyl-2-chloro-2-deoxy-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-(N-fluorenylmethoxycarbonyl-β-alanyl)-amido-β-D-glucopyranoside

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Chemical Property of methyl (2,3,4-tri-O-benzyl-α-L-mannopyranosyl)-(1->3)-(4-O-benzyl-2-chloro-2-deoxy-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-(N-fluorenylmethoxycarbonyl-β-alanyl)-amido-β-D-glucopyranoside

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Technology Process of methyl (2,3,4-tri-O-benzyl-α-L-mannopyranosyl)-(1->3)-(4-O-benzyl-2-chloro-2-deoxy-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-(N-fluorenylmethoxycarbonyl-β-alanyl)-amido-β-D-glucopyranoside

There total 14 articles about methyl (2,3,4-tri-O-benzyl-α-L-mannopyranosyl)-(1->3)-(4-O-benzyl-2-chloro-2-deoxy-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-(N-fluorenylmethoxycarbonyl-β-alanyl)-amido-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:

: Benzoic acid (2S,3S,4R)-3-benzyloxy-5,6-dichloro-2-methyl-tetrahydro-pyran-4-yl ester

: 864815-52-1
methyl (2,3,4-tri-O-benzyl-α-L-mannopyranosyl)-(1->3)-(4-O-benzyl-2-chloro-2-deoxy-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-(N-fluorenylmethoxycarbonyl-β-alanyl)-amido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1.1: 1.99 g / AgOAc / 12 h / 20 °C

2.1: 91 percent / 3 Angstroem molecular sieves; BF₃*OEt₂ / CH₂Cl₂ / 2 h

3.1: 3 Angstroem molecular sieves / CH₂Cl₂ / 1 h

3.2: 92 percent / NIS; AgOTf / CH₂Cl₂ / 0.25 h

4.1: 81 percent / NaOMe; MeOH / CH₂Cl₂ / 12 h / 20 °C

5.1: 86 percent / NIS; TfOH / CH₂Cl₂ / 2 h / -20 °C

6.1: aq. NH₂NH₂ / ethanol / 24 h / Heating

7.1: TBAF / tetrahydrofuran / 24 h

8.1: 0.510 g / TBTU; HOBt; N-ethylmorpholine / dimethylformamide / 2 h

With N-ethylmorpholine;; methanol; N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; silver(I) acetate; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; hydrazine hydrate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Koenig-Knorr glycosylation;
DOI:10.1039/b416106h

Reference yield:

: 864815-47-4
phenyl 6-O-(tert-butyldimethylsilyl)-1-thio-α-L-mannopyranoside

: 864815-52-1
methyl (2,3,4-tri-O-benzyl-α-L-mannopyranosyl)-(1->3)-(4-O-benzyl-2-chloro-2-deoxy-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-(N-fluorenylmethoxycarbonyl-β-alanyl)-amido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 94 percent / dimethylformamide / 16 h

2.1: 86 percent / NIS; TfOH / CH₂Cl₂ / 2 h / -20 °C

3.1: aq. NH₂NH₂ / ethanol / 24 h / Heating

4.1: TBAF / tetrahydrofuran / 24 h

5.1: 0.510 g / TBTU; HOBt; N-ethylmorpholine / dimethylformamide / 2 h

With N-ethylmorpholine;; N-iodo-succinimide; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; sodium hydride; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; hydrazine hydrate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/b416106h

Reference yield:

: Benzoic acid (4R,5S,6S)-2-acetoxy-5-benzyloxy-3-chloro-6-methyl-tetrahydro-pyran-4-yl ester

: 864815-52-1
methyl (2,3,4-tri-O-benzyl-α-L-mannopyranosyl)-(1->3)-(4-O-benzyl-2-chloro-2-deoxy-α-L-rhamnopyranosyl)-(1->3)-4,6-O-benzylidene-2-deoxy-2-(N-fluorenylmethoxycarbonyl-β-alanyl)-amido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: 91 percent / 3 Angstroem molecular sieves; BF₃*OEt₂ / CH₂Cl₂ / 2 h

2.1: 3 Angstroem molecular sieves / CH₂Cl₂ / 1 h

2.2: 92 percent / NIS; AgOTf / CH₂Cl₂ / 0.25 h

3.1: 81 percent / NaOMe; MeOH / CH₂Cl₂ / 12 h / 20 °C

4.1: 86 percent / NIS; TfOH / CH₂Cl₂ / 2 h / -20 °C

5.1: aq. NH₂NH₂ / ethanol / 24 h / Heating

6.1: TBAF / tetrahydrofuran / 24 h

7.1: 0.510 g / TBTU; HOBt; N-ethylmorpholine / dimethylformamide / 2 h

With N-ethylmorpholine;; methanol; N-iodo-succinimide; trifluorormethanesulfonic acid; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; hydrazine hydrate; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/b416106h