ethyl 2-O-benzoyl-3,4-dideoxy-3,4-diazido-6-O-chloroacetyl-1-thio-β-D-allopyranoside

Base Information

Chemical Name:ethyl 2-O-benzoyl-3,4-dideoxy-3,4-diazido-6-O-chloroacetyl-1-thio-β-D-allopyranoside
CAS No.:620172-01-2
Molecular Formula:C₁₇H₁₉ClN₆O₅S
Molecular Weight:454.894
Hs Code.:

Synonyms:ethyl 2-O-benzoyl-3,4-dideoxy-3,4-diazido-6-O-chloroacetyl-1-thio-β-D-allopyranoside

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Chemical Property of ethyl 2-O-benzoyl-3,4-dideoxy-3,4-diazido-6-O-chloroacetyl-1-thio-β-D-allopyranoside

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Technology Process of ethyl 2-O-benzoyl-3,4-dideoxy-3,4-diazido-6-O-chloroacetyl-1-thio-β-D-allopyranoside

There total 8 articles about ethyl 2-O-benzoyl-3,4-dideoxy-3,4-diazido-6-O-chloroacetyl-1-thio-β-D-allopyranoside 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:

: 79-04-9
chloroacetyl chloride

: 620172-09-0
Benzoic acid (2S,3R,4R,5S,6S)-4,5-diazido-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-tetrahydro-pyran-3-yl ester

: 620172-01-2
ethyl 2-O-benzoyl-3,4-dideoxy-3,4-diazido-6-O-chloroacetyl-1-thio-β-D-allopyranoside

Guidance literature:: Benzoic acid (2S,3R,4R,5S,6S)-4,5-diazido-6-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-tetrahydro-pyran-3-yl ester; With pyridine; hydrogen fluoride; at 0 ℃; for 0.25h;

chloroacetyl chloride; With pyridine; dmap; for 0.416667h;

Reference yield:

: 56245-60-4,686299-00-3
ethyl 1-thio-β-D-galactopyranoside

: 620172-01-2
ethyl 2-O-benzoyl-3,4-dideoxy-3,4-diazido-6-O-chloroacetyl-1-thio-β-D-allopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: DMAP / pyridine / 0.5 h / 60 °C

2.1: camphorsulfonic acid / acetone / 3 h / 20 °C

3.1: DMAP / pyridine / 4 h / 20 °C

4.1: 4.34 g / AcOH / tetrahydrofuran; H₂O / 5 h / 60 °C

5.1: Tf₂O; pyridine / CH₂Cl₂ / 0.25 h / 0 °C

5.2: 63 percent / NaN₃; HMPA / CH₂Cl₂; dimethylformamide / 3 h / 50 °C

6.1: HF*Py / pyridine / 5 h / 0 °C

7.1: 777 mg / DMAP; pyridine / 0.42 h

With pyridine; dmap; trifluoromethylsulfonic anhydride; camphor-10-sulfonic acid; pyridine hydrogenfluoride; acetic acid; In tetrahydrofuran; pyridine; dichloromethane; water; acetone;
DOI:10.1021/ol035213i

Reference yield:

: ethyl 6-O-(tert-butyldiphenylsilyl)-1-thio-β-D-galactopyranoside

: 620172-01-2
ethyl 2-O-benzoyl-3,4-dideoxy-3,4-diazido-6-O-chloroacetyl-1-thio-β-D-allopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: camphorsulfonic acid / acetone / 3 h / 20 °C

2.1: DMAP / pyridine / 4 h / 20 °C

3.1: 4.34 g / AcOH / tetrahydrofuran; H₂O / 5 h / 60 °C

4.1: Tf₂O; pyridine / CH₂Cl₂ / 0.25 h / 0 °C

4.2: 63 percent / NaN₃; HMPA / CH₂Cl₂; dimethylformamide / 3 h / 50 °C

5.1: HF*Py / pyridine / 5 h / 0 °C

6.1: 777 mg / DMAP; pyridine / 0.42 h

With pyridine; dmap; trifluoromethylsulfonic anhydride; camphor-10-sulfonic acid; pyridine hydrogenfluoride; acetic acid; In tetrahydrofuran; pyridine; dichloromethane; water; acetone;
DOI:10.1021/ol035213i