methyl 2,4,6-tri-O-benzyl-3-O-(2,3,6-tri-O-benzyl-4-O-picoloyl-α-D-glucopyranosyl)-α-D-glucopyranoside

Base Information

Chemical Name:methyl 2,4,6-tri-O-benzyl-3-O-(2,3,6-tri-O-benzyl-4-O-picoloyl-α-D-glucopyranosyl)-α-D-glucopyranoside
CAS No.:1415590-89-4
Molecular Formula:C₆₁H₆₃NO₁₂
Molecular Weight:1002.17
Hs Code.:

Synonyms:methyl 2,4,6-tri-O-benzyl-3-O-(2,3,6-tri-O-benzyl-4-O-picoloyl-α-D-glucopyranosyl)-α-D-glucopyranoside

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Chemical Property of methyl 2,4,6-tri-O-benzyl-3-O-(2,3,6-tri-O-benzyl-4-O-picoloyl-α-D-glucopyranosyl)-α-D-glucopyranoside

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Technology Process of methyl 2,4,6-tri-O-benzyl-3-O-(2,3,6-tri-O-benzyl-4-O-picoloyl-α-D-glucopyranosyl)-α-D-glucopyranoside

There total 6 articles about methyl 2,4,6-tri-O-benzyl-3-O-(2,3,6-tri-O-benzyl-4-O-picoloyl-α-D-glucopyranosyl)-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: 94.0%

: 35303-86-7
(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol

: 1415590-57-6
ethyl 2,3,6-tri-O-benzyl-4-O-picoloyl-1-thio-β-D-glucopyranoside

: 1415590-89-4
methyl 2,4,6-tri-O-benzyl-3-O-(2,3,6-tri-O-benzyl-4-O-picoloyl-α-D-glucopyranosyl)-α-D-glucopyranoside

Guidance literature:: (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol; ethyl 2,3,6-tri-O-benzyl-4-O-picoloyl-1-thio-β-D-glucopyranoside; In 1,2-dichloro-ethane; for 1h; Molecular sieve; Inert atmosphere;

With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In 1,2-dichloro-ethane; at -30 - 42 ℃; for 7h;
DOI:10.1021/ja307355n

Reference yield:

: 35303-86-7
(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol

: 1415590-57-6
ethyl 2,3,6-tri-O-benzyl-4-O-picoloyl-1-thio-β-D-glucopyranoside

: 1415590-89-4
methyl 2,4,6-tri-O-benzyl-3-O-(2,3,6-tri-O-benzyl-4-O-picoloyl-α-D-glucopyranosyl)-α-D-glucopyranoside

: 1415590-90-7
methyl 2,4,6-tri-O-benzyl-3-O-(2,3,6-tri-O-benzyl-4-O-picoloyl-β-D-glucopyranosyl)-α-D-glucopyranoside

Guidance literature:: (2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol; ethyl 2,3,6-tri-O-benzyl-4-O-picoloyl-1-thio-β-D-glucopyranoside; In 1,2-dichloro-ethane; for 1h; Molecular sieve; Inert atmosphere;

With dimethyl-(methylthio)-sulphonium trifluoromethanesulphonate; In 1,2-dichloro-ethane; at -30 - 42 ℃; for 7h; Overall yield = 87%; Optical yield = 81.818 %de;
DOI:10.1021/ja307355n

Reference yield:

: 141263-02-7
ethyl 2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

: 1415590-89-4
methyl 2,4,6-tri-O-benzyl-3-O-(2,3,6-tri-O-benzyl-4-O-picoloyl-α-D-glucopyranosyl)-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

2.1: 1,2-dichloro-ethane / 1 h / Molecular sieve; Inert atmosphere

2.2: 7 h / -30 - 42 °C

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/ja307355n