methyl 6-O-[(tert-butyl)dimethylsilyl]-3,4-bis-O-(4-methoxybenzyl)-2-O-{[2-(trimethylsilyl)ethoxy]methyl}-α-D-allopyranoside

Base Information

• Chemical Name: methyl 6-O-[(tert-butyl)dimethylsilyl]-3,4-bis-O-(4-methoxybenzyl)-2-O-{[2-(trimethylsilyl)ethoxy]methyl}-α-D-allopyranoside
• CAS No.: 863554-26-1
• Molecular Formula: C₃₅H₅₈O₉Si₂
• Molecular Weight: 679.011
• Mol file: 863554-26-1.mol

Synonyms:methyl 6-O-[(tert-butyl)dimethylsilyl]-3,4-bis-O-(4-methoxybenzyl)-2-O-{[2-(trimethylsilyl)ethoxy]methyl}-α-D-allopyranoside

Chemical Property of methyl 6-O-[(tert-butyl)dimethylsilyl]-3,4-bis-O-(4-methoxybenzyl)-2-O-{[2-(trimethylsilyl)ethoxy]methyl}-α-D-allopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-O-[(tert-butyl)dimethylsilyl]-3,4-bis-O-(4-methoxybenzyl)-2-O-{[2-(trimethylsilyl)ethoxy]methyl}-α-D-allopyranoside

There total 11 articles about methyl 6-O-[(tert-butyl)dimethylsilyl]-3,4-bis-O-(4-methoxybenzyl)-2-O-{[2-(trimethylsilyl)ethoxy]methyl}-α-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: 70.0%

methyl 6-O-[(tert-butyl)dimethylsilyl]-2-O-{[2-(trimethylsilyl)ethoxy]methyl}-α-D-allopyranoside (863554-25-0) + p-Methoxybenzyl bromide (2746-25-0) → methyl 6-O-[(tert-butyl)dimethylsilyl]-3,4-bis-O-(4-methoxybenzyl)-2-O-{[2-(trimethylsilyl)ethoxy]methyl}-α-D-allopyranoside (863554-26-1)

Guidance literature:

methyl 6-O-[(tert-butyl)dimethylsilyl]-2-O-{[2-(trimethylsilyl)ethoxy]methyl}-α-D-allopyranoside; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 1h;

p-Methoxybenzyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; for 72h;

DOI:10.1002/hlca.200590099

Reference yield:

(3aR,4R,6S,7aR)-4-Benzyloxymethyl-6-methoxy-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one (863554-17-0) → methyl 6-O-[(tert-butyl)dimethylsilyl]-3,4-bis-O-(4-methoxybenzyl)-2-O-{[2-(trimethylsilyl)ethoxy]methyl}-α-D-allopyranoside (863554-26-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 88 percent / NaBH₄ / ethanol / 0.5 h / 0 °C

2.1: 80 percent / KH / tetrahydrofuran / 1 h

3.1: 80 percent / acetic acid; H₂O / 4.5 h / 20 °C

4.1: 84 percent / H₂ / Pd/C / ethanol / 1 h

5.1: 90 percent / 1H-imidazole / CH₂Cl₂ / 1 h

6.1: sodium hexamethyldisilazanide / tetrahydrofuran / 1 h / 0 °C

6.2: 70 percent / Bu₄NI / tetrahydrofuran / 72 h

With 1H-imidazole; sodium tetrahydroborate; hydrogen; sodium hexamethyldisilazane; potassium hydride; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; acetic acid;

DOI:10.1002/hlca.200590099

Reference yield:

methyl 6-O-benzyl-3,4-O-isopropylidene-α-D-altropyranoside (863554-22-7) → methyl 6-O-[(tert-butyl)dimethylsilyl]-3,4-bis-O-(4-methoxybenzyl)-2-O-{[2-(trimethylsilyl)ethoxy]methyl}-α-D-allopyranoside (863554-26-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 100 percent / 4-methylmorpholine 4-oxide; tetrapropylammonium perruthenate / CH₂Cl₂ / 1 h

2.1: 88 percent / NaBH₄ / ethanol / 0.5 h / 0 °C

3.1: 80 percent / KH / tetrahydrofuran / 1 h

4.1: 80 percent / acetic acid; H₂O / 4.5 h / 20 °C

5.1: 84 percent / H₂ / Pd/C / ethanol / 1 h

6.1: 90 percent / 1H-imidazole / CH₂Cl₂ / 1 h

7.1: sodium hexamethyldisilazanide / tetrahydrofuran / 1 h / 0 °C

7.2: 70 percent / Bu₄NI / tetrahydrofuran / 72 h

With 1H-imidazole; sodium tetrahydroborate; tetrapropylammonium perruthennate; hydrogen; sodium hexamethyldisilazane; potassium hydride; 4-methylmorpholine N-oxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; acetic acid;

DOI:10.1002/hlca.200590099

upstream raw materials:

methyl 6-O-[(tert-butyl)dimethylsilyl]-2-O-{[2-(trimethylsilyl)ethoxy]methyl}-α-D-allopyranoside

p-Methoxybenzyl bromide

(3aR,4R,6S,7aR)-4-Benzyloxymethyl-6-methoxy-2,2-dimethyl-dihydro-[1,3]dioxolo[4,5-c]pyran-7-one

methyl 6-O-benzyl-3,4-O-isopropylidene-α-D-altropyranoside

Downstream raw materials:

methyl 3,4-bis-O-(4-methoxybenzyl)-2-O-{[2-(trimethylsilyl)ethoxy]methyl}-α-D-allopyranoside