O-[2-Azido-2-deoxy-4,6-O-[(S)-phenylmethylene]-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-alpha-D-galactopyranosyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-threonine 1,1-dimethylethyl ester

Base Information

Chemical Name:O-[2-Azido-2-deoxy-4,6-O-[(S)-phenylmethylene]-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-alpha-D-galactopyranosyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-threonine 1,1-dimethylethyl ester
CAS No.:195976-08-0
Molecular Formula:C50H58N4O18
Molecular Weight:1003.03
Hs Code.:

O-[2-Azido-2-deoxy-4,6-O-[(S)-phenylmethylene]-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-alpha-D-galactopyranosyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-threonine 1,1-dimethylethyl ester

Synonyms:O-[2-Azido-2-deoxy-4,6-O-[(S)-phenylmethylene]-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-alpha-D-galactopyranosyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-threonine 1,1-dimethylethyl ester

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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 O-[2-Azido-2-deoxy-4,6-O-[(S)-phenylmethylene]-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-alpha-D-galactopyranosyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-threonine 1,1-dimethylethyl ester

Chemical Property:

Purity/Quality:: 95% ^*data from raw suppliers

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Technology Process of O-[2-Azido-2-deoxy-4,6-O-[(S)-phenylmethylene]-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-alpha-D-galactopyranosyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-threonine 1,1-dimethylethyl ester

There total 7 articles about O-[2-Azido-2-deoxy-4,6-O-[(S)-phenylmethylene]-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-alpha-D-galactopyranosyl]-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-threonine 1,1-dimethylethyl 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: 80.0%

: 86520-63-0
2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate

: 195976-07-9
N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-(2-azido-2-deoxy-4,6-O-benzylidene-α-D-galactopyranosyl)-L-threonine tert-butyl ester

: 195976-08-0
N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-[O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-galactopyranosyl)-(1''-3)-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)]-L-threonine tert-butyl ester

Guidance literature:: 2,3,4,6-tetra-O-acetyl-α-galactopyranosyl trichloroacetimidate; N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-(2-azido-2-deoxy-4,6-O-benzylidene-α-D-galactopyranosyl)-L-threonine tert-butyl ester; In 1,2-dichloro-ethane; at 20 ℃; for 0.5h; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; at -20 ℃; for 1h; Molecular sieve;
DOI:10.1021/ol402845e

Reference yield: 61.0%

: C₃₈H₄₂N₄O₁₀

: 74808-10-9,86520-63-0,87119-53-7,92052-29-4,121238-27-5,142831-80-9,127061-80-7
2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate

: 195976-08-0
N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-[O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-galactopyranosyl)-(1''-3)-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)]-L-threonine tert-butyl ester

Guidance literature:: C₃₈H₄₂N₄O₁₀; 2,3,4,6-tetra-O-acetyl-D-galactopyranosyl trichloroacetimidate; In dichloromethane; at 0 ℃; for 2h; Molecular sieve; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.carres.2010.05.004

Reference yield:

: 195976-26-2
(2S,3R)-3-((2S,3R,4R,5R,6R)-3-Azido-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-butyric acid tert-butyl ester

: 195976-08-0
N-[(9H-fluoren-9-yl)-methoxycarbonyl]-O-[O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-galactopyranosyl)-(1''-3)-(2-azido-4O,6O-benzylidene-2-deoxy-α-D-galactopyranosyl)]-L-threonine tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 65 percent / p-TsOH / nitromethane / 1 h / Ambient temperature

2: 68 percent / MS 4A, TMSOTf / 1,2-dichloro-ethane / 0 °C / 1.) 1 h, 2.) 45 min

With trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; In nitromethane; 1,2-dichloro-ethane;
DOI:10.1039/a701742a