methyl 3-O-benzyl-2-deoxy-6-O-(diphenyl-t-butylsilyl)-2-C-methyl-α-D-arabino-hexapyranosid-4-ulose

Base Information

• Chemical Name: methyl 3-O-benzyl-2-deoxy-6-O-(diphenyl-t-butylsilyl)-2-C-methyl-α-D-arabino-hexapyranosid-4-ulose
• CAS No.: 109914-93-4
• Molecular Formula: C₃₁H₃₈O₅Si
• Molecular Weight: 518.725
• Mol file: 109914-93-4.mol

Synonyms:methyl 3-O-benzyl-2-deoxy-6-O-(diphenyl-t-butylsilyl)-2-C-methyl-α-D-arabino-hexapyranosid-4-ulose

Chemical Property of methyl 3-O-benzyl-2-deoxy-6-O-(diphenyl-t-butylsilyl)-2-C-methyl-α-D-arabino-hexapyranosid-4-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-2-deoxy-6-O-(diphenyl-t-butylsilyl)-2-C-methyl-α-D-arabino-hexapyranosid-4-ulose

There total 6 articles about methyl 3-O-benzyl-2-deoxy-6-O-(diphenyl-t-butylsilyl)-2-C-methyl-α-D-arabino-hexapyranosid-4-ulose 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: 86.0%

methyl 3-O-benzyl-2-deoxy-6-O-(diphenyl-t-butylsilyl)-2-C-methyl-α-D-altropyranoside (109914-90-1) → methyl 3-O-benzyl-2-deoxy-6-O-(diphenyl-t-butylsilyl)-2-C-methyl-α-D-arabino-hexapyranosid-4-ulose (109914-93-4)

Guidance literature:

With Chloro-oxo-acetic acid; dimethyl sulfoxide; In dichloromethane; at -60 ℃; for 4h;

Reference yield:

methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside (2880-96-8,3150-15-0,3150-16-1,3257-59-8,14187-71-4,15384-57-3,19465-13-5,32976-15-1,52885-37-7,53270-02-3,53270-03-4,65391-11-9,65391-12-0,66537-92-6,67226-04-4,71184-14-0,86420-78-2,86420-79-3,91177-51-4,91177-52-5,117708-93-7,120408-72-2) → methyl 3-O-benzyl-2-deoxy-6-O-(diphenyl-t-butylsilyl)-2-C-methyl-α-D-arabino-hexapyranosid-4-ulose (109914-93-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 56 percent / Cu(I)I / diethyl ether / 5 h / 0 °C

2: 94 percent / NaH / tetrahydrofuran / 18 h / Heating

3: 85 percent / toluene-p-sulphonic acid monohydrate / methanol / 3 h / 0 °C

4: 97 percent / imidazole / dimethylformamide / 12 h

5: 86 percent / oxalylchloride, DMSO / CH₂Cl₂ / 4 h / -60 °C

With 1H-imidazole; copper(l) iodide; Chloro-oxo-acetic acid; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

benzyl chloride (100-44-7) → methyl 3-O-benzyl-2-deoxy-6-O-(diphenyl-t-butylsilyl)-2-C-methyl-α-D-arabino-hexapyranosid-4-ulose (109914-93-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / NaH / tetrahydrofuran / 18 h / Heating

2: 85 percent / toluene-p-sulphonic acid monohydrate / methanol / 3 h / 0 °C

3: 97 percent / imidazole / dimethylformamide / 12 h

4: 86 percent / oxalylchloride, DMSO / CH₂Cl₂ / 4 h / -60 °C

With 1H-imidazole; Chloro-oxo-acetic acid; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

methyl 3-O-benzyl-2-deoxy-6-O-(diphenyl-t-butylsilyl)-2-C-methyl-α-D-altropyranoside

benzyl chloride

methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altropyranoside

methyl 3-O-benzyl-2-deoxy-2-C-methyl-α-D-altropyranoside

Downstream raw materials:

methyl 3-O-benzyl-2,4-dideoxy-6-O-(diphenyl-t-butylsilyl)-2-C-methyl-4-C-methylene-α-D-arabino-hexopyranoside

O-(diphenyl-t-butylsilyl)-2-C-methyl-α-D-idopyranoside

methyl 3-O-benzyl-2-deoxy-6-O-(diphenyl-t-butylsilyl)-2-C-methyl-α-D-altropyranoside

methyl 3-O-benzyl-2-deoxy-6-O-(diphenyl-t-butylsilyl)-2-C-methyl-4-C-(trimethylsilylmethyl)-α-D-altro-pyranoside