3,6-di-O-acetyl-4-O-benzyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranosyl trichloroacetimidate

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Chemical Name:3,6-di-O-acetyl-4-O-benzyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranosyl trichloroacetimidate
CAS No.:865859-90-1
Molecular Formula:C₃₃H₃₄Cl₃NO₈S
Molecular Weight:711.06
Hs Code.:

Synonyms:3,6-di-O-acetyl-4-O-benzyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranosyl trichloroacetimidate

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Chemical Property of 3,6-di-O-acetyl-4-O-benzyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranosyl trichloroacetimidate

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Technology Process of 3,6-di-O-acetyl-4-O-benzyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranosyl trichloroacetimidate

There total 14 articles about 3,6-di-O-acetyl-4-O-benzyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-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: 93.0%

: 3,6-di-O-acetyl-4-O-benzyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-D-glucopyranose

: 545-06-2
trichloroacetonitrile

: 865859-90-1
3,6-di-O-acetyl-4-O-benzyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/ja052548h

Reference yield:

: 865860-15-7
1,6-anhydro-4-O-benzyl-2-O-{(S)-2-(hydroxymethyl)benzyl}-β-D-glucopyranose

: 865859-90-1
3,6-di-O-acetyl-4-O-benzyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / pyridine / 2 h / 20 °C

2: 96 percent / tetrahydrofuran / 2 h / 20 °C

3: 90 percent / trimethylsilyl trifluoromethanesulfonate / -50 - -20 °C

4: 90 percent / hydrazine acetate / dimethylformamide / 20 °C

5: 93 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 0 °C

With pyridine; trimethylsilyl trifluoromethanesulfonate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja052548h

Reference yield:

: 849619-42-7
1,6-anhydro-4-O-benzyl-2-O-[(S)-α-(ethoxycarbonyl)benzyl]-β-D-glucopyranose

: 865859-90-1
3,6-di-O-acetyl-4-O-benzyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / LiAlH₄ / tetrahydrofuran / 4 h / Heating

2: 93 percent / pyridine / 2 h / 20 °C

3: 96 percent / tetrahydrofuran / 2 h / 20 °C

4: 90 percent / trimethylsilyl trifluoromethanesulfonate / -50 - -20 °C

5: 90 percent / hydrazine acetate / dimethylformamide / 20 °C

6: 93 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 0 °C

With pyridine; lithium aluminium tetrahydride; trimethylsilyl trifluoromethanesulfonate; hydrazinium monoacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja052548h