dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-α-D-glucopyranoside

Base Information

Chemical Name:dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-α-D-glucopyranoside
CAS No.:197164-88-8
Molecular Formula:C₇₄H₈₆O₁₀S
Molecular Weight:1167.56
Hs Code.:

Synonyms:dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-α-D-glucopyranoside

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Chemical Property of dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-α-D-glucopyranoside

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Technology Process of dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-α-D-glucopyranoside

There total 7 articles about dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-α-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: 40.0%

: 74666-83-4,105990-37-2,125354-46-3,125354-47-4,125411-99-6,108739-67-9
1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside

: 197164-80-0
((2R,3R,4S,5R,6R)-3,4,5-Tris-benzyloxy-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-2-yl)-methanol

: 197164-88-8
dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-α-D-glucopyranoside

Guidance literature:: With iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 Angstroem MS; In diethyl ether; dichloromethane; for 1h; Ambient temperature;
DOI:10.1021/jo971233k

Reference yield:

: Dicyclohexyl-methanethiol

: 197164-88-8
dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 49 percent / TMSOTf / CH₂Cl₂ / 16 h / Ambient temperature

2: 100 percent / NaOMe / CH₂Cl₂; methanol / 3 h

3: 76 percent / pyridine / 18 h / Ambient temperature

4: 92 percent / NaH / dimethylformamide / 18 h / Ambient temperature

5: 76 percent / acetic acid; H₂O / 18 h / 60 °C

6: 40 percent / 4 Angstroem MS, iodonium dicollidine perchlorate / CH₂Cl₂; diethyl ether / 1 h / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 Angstroem MS; sodium methylate; sodium hydride; In pyridine; methanol; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jo971233k

Reference yield:

: 171503-78-9
Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-dicyclohexylmethylsulfanyl-tetrahydro-pyran-4-yl ester

: 197164-88-8
dicyclohexylmethyl 2,3,4-tri-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-thio-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / NaOMe / CH₂Cl₂; methanol / 3 h

2: 76 percent / pyridine / 18 h / Ambient temperature

3: 92 percent / NaH / dimethylformamide / 18 h / Ambient temperature

4: 76 percent / acetic acid; H₂O / 18 h / 60 °C

5: 40 percent / 4 Angstroem MS, iodonium dicollidine perchlorate / CH₂Cl₂; diethyl ether / 1 h / Ambient temperature

With iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 Angstroem MS; sodium methylate; sodium hydride; In pyridine; methanol; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jo971233k