Acetic acid (2S,3S,4S,5R,6R)-6-azidomethyl-4,5-bis-benzyloxy-2-[3-(9H-fluoren-9-ylmethoxycarbonylamino)-propoxy]-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2S,3S,4S,5R,6R)-6-azidomethyl-4,5-bis-benzyloxy-2-[3-(9H-fluoren-9-ylmethoxycarbonylamino)-propoxy]-tetrahydro-pyran-3-yl ester
CAS No.:674302-98-8
Molecular Formula:C₄₀H₄₂N₄O₈
Molecular Weight:706.795
Hs Code.:

Synonyms:Acetic acid (2S,3S,4S,5R,6R)-6-azidomethyl-4,5-bis-benzyloxy-2-[3-(9H-fluoren-9-ylmethoxycarbonylamino)-propoxy]-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2S,3S,4S,5R,6R)-6-azidomethyl-4,5-bis-benzyloxy-2-[3-(9H-fluoren-9-ylmethoxycarbonylamino)-propoxy]-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3S,4S,5R,6R)-6-azidomethyl-4,5-bis-benzyloxy-2-[3-(9H-fluoren-9-ylmethoxycarbonylamino)-propoxy]-tetrahydro-pyran-3-yl ester

There total 6 articles about Acetic acid (2S,3S,4S,5R,6R)-6-azidomethyl-4,5-bis-benzyloxy-2-[3-(9H-fluoren-9-ylmethoxycarbonylamino)-propoxy]-tetrahydro-pyran-3-yl ester 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: 60.0%

: 157887-82-6
9H-fluoren-9-ylmethyl N-(3-hydroxypropyl)carbamate

: 674302-97-7
6-azdio-3,4-di-O-benzyl-6-deoxy-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

: methyl 2-O-acetyl-6-azido-3,4-di-O-benzyl-6-deoxy-α-D-mannopyranoside

: 674302-99-9
[3-((2S,3S,4R,5R,6R)-6-Azidomethyl-4,5-bis-benzyloxy-3-hydroxy-tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid 9H-fluoren-9-ylmethyl ester

: 674302-98-8
Acetic acid (2S,3S,4S,5R,6R)-6-azidomethyl-4,5-bis-benzyloxy-2-[3-(9H-fluoren-9-ylmethoxycarbonylamino)-propoxy]-tetrahydro-pyran-3-yl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1002/ejoc.200300483

Reference yield:

: 100-39-0
benzyl bromide

: 674302-98-8
Acetic acid (2S,3S,4S,5R,6R)-6-azidomethyl-4,5-bis-benzyloxy-2-[3-(9H-fluoren-9-ylmethoxycarbonylamino)-propoxy]-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 3.29 g / NaH; TBAI / dimethylformamide / 0 - 20 °C

2: TBAF / tetrahydrofuran / 3 h / -78 - 20 °C

3: pyridine / 0.75 h / 0 °C

4: 744 mg / NaN₃ / dimethylformamide / 80 °C

5: 23 percent / TMSOTf / CH₂Cl₂ / 1 h / 0 °C

6: pyridine / 1 h

With pyridine; sodium azide; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200300483

Reference yield:

: 152174-59-9
3,4-di-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranoside

: 674302-98-8
Acetic acid (2S,3S,4S,5R,6R)-6-azidomethyl-4,5-bis-benzyloxy-2-[3-(9H-fluoren-9-ylmethoxycarbonylamino)-propoxy]-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine / 0.75 h / 0 °C

2: 744 mg / NaN₃ / dimethylformamide / 80 °C

3: 23 percent / TMSOTf / CH₂Cl₂ / 1 h / 0 °C

4: pyridine / 1 h

With pyridine; sodium azide; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/ejoc.200300483