phenyl 3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
CAS No.:263010-75-9
Molecular Formula:C₂₄H₃₁Cl₃N₂O₉S
Molecular Weight:629.943
Hs Code.:

Synonyms:phenyl 3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

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Chemical Property of phenyl 3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

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Technology Process of phenyl 3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

There total 6 articles about phenyl 3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-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: 47.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 263010-74-8
phenyl 3,4-di-O-acetyl-6-azido-2,6-dideoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

: 263010-75-9
phenyl 3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Guidance literature:: With hydrogen; platinum(IV) oxide; In ethyl acetate; at 40 - 50 ℃; for 18h;
DOI:10.1248/cpb.48.32

Reference yield:

: 172490-46-9
2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose

: 263010-75-9
phenyl 3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / CH₂Cl₂ / 2 h / 20 °C

2: 13.5 g / pyridine / 5 h / 20 °C

3: 61 percent / NaN₃; 18-crown-6 / dimethylformamide / 40 h / 40 - 50 °C

4: 61 percent / BF₃*OEt / CH₂Cl₂ / 24 h / 20 °C

5: 47 percent / H₂ / PtO₂ / ethyl acetate / 18 h / 40 - 50 °C

With pyridine; sodium azide; 18-crown-6 ether; boron trifluoride diethyl etherate; hydrogen; platinum(IV) oxide; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1: tosylation / 2: Acetylation / 3: Substitution / 4: thioglycosidation / 5: Reduction;
DOI:10.1248/cpb.48.32

Reference yield:

: 108-98-5
thiophenol

: 263010-75-9
phenyl 3,4-di-O-acetyl-6-(tert-butoxycarbonylamino)-2,6-dideoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 61 percent / BF₃*OEt / CH₂Cl₂ / 24 h / 20 °C

2: 47 percent / H₂ / PtO₂ / ethyl acetate / 18 h / 40 - 50 °C

With boron trifluoride diethyl etherate; hydrogen; platinum(IV) oxide; In dichloromethane; ethyl acetate; 1: thioglycosidation / 2: Reduction;
DOI:10.1248/cpb.48.32