(2-methyl-5-tert-butylphenyl)-4-O-benzyl-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:(2-methyl-5-tert-butylphenyl)-4-O-benzyl-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside
CAS No.:1456773-44-6
Molecular Formula:C₃₅H₅₄O₆SSi
Molecular Weight:630.962
Hs Code.:

Synonyms:(2-methyl-5-tert-butylphenyl)-4-O-benzyl-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

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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-methyl-5-tert-butylphenyl)-4-O-benzyl-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

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Technology Process of (2-methyl-5-tert-butylphenyl)-4-O-benzyl-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

There total 7 articles about (2-methyl-5-tert-butylphenyl)-4-O-benzyl-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-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: 97.0%

: 1456773-41-3
(2-methyl-5-tert-butylphenyl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

: 1456773-44-6
(2-methyl-5-tert-butylphenyl)-4-O-benzyl-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

Guidance literature:: With borane-THF; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 - 20 ℃; regioselective reaction; Inert atmosphere;
DOI:10.1002/chem.201204518

Reference yield:

: 1334540-33-8
(2-methyl-5-tert-butylphenyl) 2,3,4,6-tetra-O-acetyl-1-S-β-D-thioglucopyranoside

: 1456773-44-6
(2-methyl-5-tert-butylphenyl)-4-O-benzyl-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: sodium methylate / methanol / Inert atmosphere

2: 10-camphorsulfonic acid / acetonitrile / Inert atmosphere

3: 1H-imidazole / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

4: pyridine; dmap / 0 - 80 °C / Inert atmosphere

5: borane-THF; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; borane-THF; trimethylsilyl trifluoromethanesulfonate; sodium methylate; 10-camphorsulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/chem.201204518

Reference yield:

: 604-69-3
β-D-glucose pentaacetate

: 1456773-44-6
(2-methyl-5-tert-butylphenyl)-4-O-benzyl-3-O-tert-butyldimethylsilyl-2-O-pivaloyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: boron trifluoride diethyl etherate / dichloromethane / Inert atmosphere

2: sodium methylate / methanol / Inert atmosphere

3: 10-camphorsulfonic acid / acetonitrile / Inert atmosphere

4: 1H-imidazole / N,N-dimethyl-formamide / 0 °C / Inert atmosphere

5: pyridine; dmap / 0 - 80 °C / Inert atmosphere

6: borane-THF; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; borane-THF; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium methylate; 10-camphorsulfonic acid; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/chem.201204518