2-(trimethylsilyl)ethyl O-(3-O-allyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-toluoyl-β-D-glucopyranoside

Base Information

• Chemical Name: 2-(trimethylsilyl)ethyl O-(3-O-allyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-toluoyl-β-D-glucopyranoside
• CAS No.: 182871-32-5
• Molecular Formula: C₆₀H₆₈O₁₆Si
• Molecular Weight: 1073.28

Synonyms:2-(trimethylsilyl)ethyl O-(3-O-allyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-toluoyl-β-D-glucopyranoside

Chemical Property of 2-(trimethylsilyl)ethyl O-(3-O-allyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-toluoyl-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(trimethylsilyl)ethyl O-(3-O-allyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-toluoyl-β-D-glucopyranoside

There total 11 articles about 2-(trimethylsilyl)ethyl O-(3-O-allyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-toluoyl-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: 87.0%

2-(trimethylsilyl)ethyl O-(3-O-allyl-6-O-levulinoyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-toluoyl-β-D-glucopyranoside (182871-24-5) → 2-(trimethylsilyl)ethyl O-(3-O-allyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-toluoyl-β-D-glucopyranoside (182871-32-5)

Guidance literature:

With methylhydrazine monoacetate; acetic acid; In toluene; for 2h; Ambient temperature;

DOI:10.1271/bbb.60.1308

Reference yield:

4-methyl-benzoyl chloride (874-60-2) → 2-(trimethylsilyl)ethyl O-(3-O-allyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-toluoyl-β-D-glucopyranoside (182871-32-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / DMAP / pyridine; 1,2-dichloro-ethane / Ambient temperature

2: 88 percent / aq. TFA / 1,2-dichloro-ethane / 1.5 h / 0 °C

3: DABCO, CMPI / tetrahydrofuran / 1.5 h / 0 °C

4: DMAP / pyridine; 1,2-dichloro-ethane / Ambient temperature

5: 98 percent / methylhydrazine acetate, AcOH / toluene / 2 h / Ambient temperature

6: 97 percent / MeOTf, AgOTf, MS₄A / 1,2-dichloro-ethane / 24 h / Ambient temperature

7: 87 percent / methylhydrazine acetate, AcOH / toluene / 2 h / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; silver trifluoromethanesulfonate; methylhydrazine monoacetate; acetic acid; trifluoroacetic acid; methyl trifluoromethanesulfonate; In tetrahydrofuran; pyridine; 1,2-dichloro-ethane; toluene;

DOI:10.1271/bbb.60.1308

Reference yield:

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-β-D-glucopyranoside (117253-03-9) → 2-(trimethylsilyl)ethyl O-(3-O-allyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-toluoyl-β-D-glucopyranoside (182871-32-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / DMAP / pyridine; 1,2-dichloro-ethane / Ambient temperature

2: 88 percent / aq. TFA / 1,2-dichloro-ethane / 1.5 h / 0 °C

3: DABCO, CMPI / tetrahydrofuran / 1.5 h / 0 °C

4: DMAP / pyridine; 1,2-dichloro-ethane / Ambient temperature

5: 98 percent / methylhydrazine acetate, AcOH / toluene / 2 h / Ambient temperature

6: 97 percent / MeOTf, AgOTf, MS₄A / 1,2-dichloro-ethane / 24 h / Ambient temperature

7: 87 percent / methylhydrazine acetate, AcOH / toluene / 2 h / Ambient temperature

With 1,4-diaza-bicyclo[2.2.2]octane; dmap; silver trifluoromethanesulfonate; methylhydrazine monoacetate; acetic acid; trifluoroacetic acid; methyl trifluoromethanesulfonate; In tetrahydrofuran; pyridine; 1,2-dichloro-ethane; toluene;

DOI:10.1271/bbb.60.1308

upstream raw materials:

2-(trimethylsilyl)ethyl O-(3-O-allyl-6-O-levulinoyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-toluoyl-β-D-glucopyranoside

4-methyl-benzoyl chloride

2-(trimethylsilyl)ethyl 4,6-O-benzylidene-β-D-glucopyranoside

4-Oxo-pentanoic acid (2R,3R,4S,5R,6R)-4-allyloxy-6-ethylsulfanyl-3,5-dihydroxy-tetrahydro-pyran-2-ylmethyl ester

Downstream raw materials:

2-(trimethylsilyl)ethyl O-(3-O-allyl-6-O-levylinoyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-toluoyl-β-D-glucopyranosyl)-(1->6)-O-(3-O-allyl-2,4-di-O-toluoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-toluoyl-β-D-glucopyranoside

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