2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

Base Information

Chemical Name:2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate
CAS No.:565462-71-7
Molecular Formula:C₃₆H₃₆Cl₃NO₅S
Molecular Weight:701.111
Hs Code.:

Synonyms:2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

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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 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

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Technology Process of 2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

There total 6 articles about 2,3,4,6-tetra-O-benzyl-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: 78.0%

: 565462-96-6
(2S,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-thiopyran-2-ol

: 545-06-2
trichloroacetonitrile

: 565462-71-7
2,3,4,6-tetra-O-benzyl-5-deoxy-5-thio-α-D-glucopyranosyl trichloroacetimidate

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

Reference yield: 57.0%

: 2,3,4,6-tetra-O-benzyl-5-thio-D-glucopyranose

: 545-06-2
trichloroacetonitrile

: 565462-71-7
2,3,4,6-tetra-O-benzyl-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

: 565462-71-7
2,3,4,6-tetra-O-benzyl-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: 88 percent / NaH / dimethylformamide / 1 h / 20 °C

4: 90 percent / HClO₄ / methanol / 3 h / 20 °C

5: 78 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 0 °C

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