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

Base Information

Chemical Name:3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranosyl trichloroacetimidate
CAS No.:865859-86-5
Molecular Formula:C₂₈H₃₀Cl₃NO₉S
Molecular Weight:662.973
Hs Code.:

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

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

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

There total 7 articles about 3,4,6-tri-O-acetyl-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: 95.0%

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

: 545-06-2
trichloroacetonitrile

: 865859-86-5
3,4,6-tri-O-acetyl-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:

: 865859-84-3
acetyl 3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranose

: 865859-86-5
3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / hydrazinium acetate / dimethylformamide / 20 °C

2: 95 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 0 °C

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

Reference yield:

: 17199-29-0
(S)-Mandelic acid

: 865859-86-5
3,4,6-tri-O-acetyl-2-O-{(1S)-phenyl-2-(phenylsulfanyl)ethyl}-α-D-glucopyranosyl trichloroacetimidate

Guidance literature:: Multi-step reaction with 7 steps

1: 72 percent / LiAlH₄ / diethyl ether / 2 h / Heating

2: 88 percent / Bu₂SnO; Et₃N / CH₂Cl₂ / 3 h / 20 °C

3: 98 percent / tetrahydrofuran / 20 °C

4: 82 percent / pyridine / 2 h / 0 °C

5: 71 percent / BF₃*OEt₂; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.5 h / 0 °C

6: 83 percent / hydrazinium acetate / dimethylformamide / 20 °C

7: 95 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 0 °C

With pyridine; lithium aluminium tetrahydride; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrazinium monoacetate; di(n-butyl)tin oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja052548h