methyl 2,3,4-tri-O-benzyl-6-O-((2S)-2-deoxy-(2-²H)-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2,3,4-tri-O-benzyl-6-O-((2S)-2-deoxy-(2-²H)-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside
• CAS No.: 1621188-74-6
• Molecular Formula: C₅₅H₈₈O₁₁Si₃
• Molecular Weight: 1010.55

Synonyms:

Chemical Property of methyl 2,3,4-tri-O-benzyl-6-O-((2S)-2-deoxy-(2-²H)-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,3,4-tri-O-benzyl-6-O-((2S)-2-deoxy-(2-²H)-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside

There total 9 articles about methyl 2,3,4-tri-O-benzyl-6-O-((2S)-2-deoxy-(2-²H)-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-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:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) + [2-2H]-1,2-dideoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose (1621188-73-5) → methyl 2,3,4-tri-O-benzyl-6-O-((2S)-2-deoxy-(2-2H)-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside (1621188-74-6) + methyl 2,3,4-tri-O-benzyl-6-O-((2S)-2-deoxy-(2-2H)-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-β-D-erythro-hexapyranosyl)-α-D-glucopyranoside

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; water; at 20 ℃; for 4h; Overall yield = 90 %; Overall yield = 92 mg; stereoselective reaction; Inert atmosphere;

DOI:10.1002/anie.201403543

Reference yield:

C14H18(2)HBrO9 → methyl 2,3,4-tri-O-benzyl-6-O-((2S)-2-deoxy-(2-2H)-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside (1621188-74-6) + methyl 2,3,4-tri-O-benzyl-6-O-((2S)-2-deoxy-(2-2H)-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-β-D-erythro-hexapyranosyl)-α-D-glucopyranoside

Guidance literature:

Multi-step reaction with 5 steps

1: zinc; sodium acetate; copper(II) sulfate / acetic acid; water / 3 h / 20 °C

2: water; methanol; triethylamine / 18 h

3: 1H-imidazole / N,N-dimethyl-formamide / 1 h / Inert atmosphere

4: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 0 - 20 °C / Inert atmosphere

5: toluene-4-sulfonic acid / dichloromethane; water / 4 h / 20 °C / Inert atmosphere

With 1H-imidazole; methanol; water; sodium acetate; toluene-4-sulfonic acid; copper(II) sulfate; triethylamine; zinc; In dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1002/anie.201403543

Reference yield:

C16H21(2)HO11 → methyl 2,3,4-tri-O-benzyl-6-O-((2S)-2-deoxy-(2-2H)-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-α-D-erythro-hexapyranosyl)-α-D-glucopyranoside (1621188-74-6) + methyl 2,3,4-tri-O-benzyl-6-O-((2S)-2-deoxy-(2-2H)-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-β-D-erythro-hexapyranosyl)-α-D-glucopyranoside

Guidance literature:

Multi-step reaction with 6 steps

1: acetic acid; hydrogen bromide / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

2: zinc; sodium acetate; copper(II) sulfate / acetic acid; water / 3 h / 20 °C

3: water; methanol; triethylamine / 18 h

4: 1H-imidazole / N,N-dimethyl-formamide / 1 h / Inert atmosphere

5: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 0 - 20 °C / Inert atmosphere

6: toluene-4-sulfonic acid / dichloromethane; water / 4 h / 20 °C / Inert atmosphere

With 1H-imidazole; methanol; water; hydrogen bromide; sodium acetate; toluene-4-sulfonic acid; copper(II) sulfate; acetic acid; triethylamine; zinc; In dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1002/anie.201403543

upstream raw materials:

1,2-dideoxy-[2-²H]-3,4,6-tri-O-acetyl-D-arabino-1-hexenopyranose

1,2-dideoxy-[2-²H]-3,4,6-tri-O-acetyl-D-arabino-1-hexenopyranose

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

[2-²H]-1,2-dideoxy-3,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-6-O-triisopropylsilyl-D-arabino-1-hexenopyranose

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