methyl 4,6-O-benzylidene-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-3-O-(4-phenylbenzoyl)-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:methyl 4,6-O-benzylidene-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-3-O-(4-phenylbenzoyl)-1-thio-β-D-glucopyranoside
CAS No.:887402-03-1
Molecular Formula:C₃₇H₃₉NO₇S
Molecular Weight:641.785
Hs Code.:

Synonyms:methyl 4,6-O-benzylidene-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-3-O-(4-phenylbenzoyl)-1-thio-β-D-glucopyranoside

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Chemical Property of methyl 4,6-O-benzylidene-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-3-O-(4-phenylbenzoyl)-1-thio-β-D-glucopyranoside

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Technology Process of methyl 4,6-O-benzylidene-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-3-O-(4-phenylbenzoyl)-1-thio-β-D-glucopyranoside

There total 12 articles about methyl 4,6-O-benzylidene-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-3-O-(4-phenylbenzoyl)-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: 84.0%

: 282525-99-9
methyl 4,6-O-benzylidene-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-1-thio-β-D-glucopyranoside

: 14002-51-8
4-biphenyl-carboxylic acid chloride

: 887402-03-1
methyl 4,6-O-benzylidene-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-3-O-(4-phenylbenzoyl)-1-thio-β-D-glucopyranoside

Guidance literature:: With dmap; In 1,2-dichloro-ethane; at 20 ℃; for 0.666667h;
DOI:10.1080/07328300500388685

Reference yield:

: 2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-D-glucopyranose

: 887402-03-1
methyl 4,6-O-benzylidene-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-3-O-(4-phenylbenzoyl)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 86 percent / pyridine / 20 °C

2: 91 percent / HBr; acetic acid / CH₂Cl₂ / 1 h / 20 °C

3: 85 percent / acetone / 0.5 h / Heating

4: 87 percent / Na₂S₂O₅ / H₂O; 1,2-dichloro-ethane / 0.33 h / 85 °C

5: 58 percent / potassium carbonate / acetone; H₂O / 2 h

6: 92 percent / sodium methoxide / methanol / 20 °C

7: 81 percent / p-toluenesulfonic acid / acetonitrile / 18 h / 60 °C

8: 84 percent / 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 0.67 h / 20 °C

With pyridine; dmap; sodium metabisulfite; hydrogen bromide; sodium methylate; potassium carbonate; toluene-4-sulfonic acid; acetic acid; In methanol; dichloromethane; water; 1,2-dichloro-ethane; acetone; acetonitrile; 6: Zemplen deacetylation;
DOI:10.1080/07328300500388685

Reference yield:

: 212394-16-6
3,4,6-tri-O-acetyl-2-deoxy-2-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)-ethylamino]-α-D-glucopyranosyl bromide

: 887402-03-1
methyl 4,6-O-benzylidene-2-deoxy-2-N-[1-(4,4-dimethyl-2,6-dioxocyclohex-1-ylidene)ethyl]amino-3-O-(4-phenylbenzoyl)-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 85 percent / acetone / 0.5 h / Heating

2: 87 percent / Na₂S₂O₅ / H₂O; 1,2-dichloro-ethane / 0.33 h / 85 °C

3: 58 percent / potassium carbonate / acetone; H₂O / 2 h

4: 92 percent / sodium methoxide / methanol / 20 °C

5: 81 percent / p-toluenesulfonic acid / acetonitrile / 18 h / 60 °C

6: 84 percent / 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 0.67 h / 20 °C

With dmap; sodium metabisulfite; sodium methylate; potassium carbonate; toluene-4-sulfonic acid; In methanol; water; 1,2-dichloro-ethane; acetone; acetonitrile; 4: Zemplen deacetylation;
DOI:10.1080/07328300500388685