2,3,4,6-[tetrakis-O-(4-methoxyphenyl)methyl]-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

Base Information

Chemical Name:2,3,4,6-[tetrakis-O-(4-methoxyphenyl)methyl]-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate
CAS No.:565462-72-8
Molecular Formula:C₄₀H₄₄Cl₃NO₉S
Molecular Weight:821.216
Hs Code.:

Synonyms:2,3,4,6-[tetrakis-O-(4-methoxyphenyl)methyl]-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

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Chemical Property of 2,3,4,6-[tetrakis-O-(4-methoxyphenyl)methyl]-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

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Technology Process of 2,3,4,6-[tetrakis-O-(4-methoxyphenyl)methyl]-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

There total 6 articles about 2,3,4,6-[tetrakis-O-(4-methoxyphenyl)methyl]-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate 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%

: 565462-97-7
(2S,3R,4S,5S,6R)-3,4,5-Tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-thiopyran-2-ol

: 545-06-2
trichloroacetonitrile

: 565462-72-8
2,3,4,6-[tetrakis-O-(4-methoxyphenyl)methyl]-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; benzene; at 0 ℃; for 1h;
DOI:10.1016/j.bmc.2005.05.028

Reference yield: 74.0%

: 545-06-2
trichloroacetonitrile

: (3R,4S,5S,6R)-3,4,5-Tris-(4-methoxy-benzyloxy)-6-(4-methoxy-benzyloxymethyl)-tetrahydro-thiopyran-2-ol

: 565462-72-8
2,3,4,6-[tetrakis-O-(4-methoxyphenyl)methyl]-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃;
DOI:10.1016/S0960-894X(03)00072-6

Reference yield:

: 137886-82-9
2,3,4,6-Tetra-O-acetyl-5-thio-α-D-glucopyranose

: 565462-72-8
2,3,4,6-[tetrakis-O-(4-methoxyphenyl)methyl]-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / p-TsOH / CH₂Cl₂ / 1.5 h / 0 °C

2: 82 percent / NaOMe / methanol / 3.5 h / 20 °C

3: 95 percent / NaH / dimethylformamide; toluene / 1 h / 20 °C

4: 81 percent / HCl / methanol / 20 °C

5: 80 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂; benzene / 1 h / 0 °C

With hydrogenchloride; sodium methylate; sodium hydride; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/j.bmc.2005.05.028