methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2-deoxy-2-C-(2-methoxycarbonylethyl)-α-D-arabino-hexosid-4-ulose

Base Information

• Chemical Name: methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2-deoxy-2-C-(2-methoxycarbonylethyl)-α-D-arabino-hexosid-4-ulose
• CAS No.: 131529-55-0
• Molecular Formula: C₂₄H₃₈O₇Si
• Molecular Weight: 466.647
• Mol file: 131529-55-0.mol

Synonyms:methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2-deoxy-2-C-(2-methoxycarbonylethyl)-α-D-arabino-hexosid-4-ulose

Chemical Property of methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2-deoxy-2-C-(2-methoxycarbonylethyl)-α-D-arabino-hexosid-4-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2-deoxy-2-C-(2-methoxycarbonylethyl)-α-D-arabino-hexosid-4-ulose

There total 9 articles about methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2-deoxy-2-C-(2-methoxycarbonylethyl)-α-D-arabino-hexosid-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: 97.0%

methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2-deoxy-2-C-(2-methoxycarbonylethyl)-α-D-altropyranoside (131529-54-9) → methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2-deoxy-2-C-(2-methoxycarbonylethyl)-α-D-arabino-hexosid-4-ulose (131529-55-0)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; for 1h;

DOI:10.1071/CH9901681

Reference yield:

methyl 4,6-O-benzylidene-2-deoxy-2-(2-propenyl)-α-D-allohexopyranoside (126108-10-9) → methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2-deoxy-2-C-(2-methoxycarbonylethyl)-α-D-arabino-hexosid-4-ulose (131529-55-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, 15 min, 2.) 17 h

3: 6.1 g / pyridinium dichromate / dimethylformamide / 22 h

4: diethyl ether / 22 h / 20 °C

5: 91 percent / camphorsulfonic acid / methanol / 5 h

6: 94 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 18 h

7: 97 percent / oxalyl chloride, dimethyl sulfoxide, Et₃N / CH₂Cl₂ / 1 h / -78 °C

With dmap; dipyridinium dichromate; oxalyl dichloride; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1071/CH9901681

Reference yield:

benzyl bromide (100-39-0) → methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2-deoxy-2-C-(2-methoxycarbonylethyl)-α-D-arabino-hexosid-4-ulose (131529-55-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, 15 min, 2.) 17 h

3: 6.1 g / pyridinium dichromate / dimethylformamide / 22 h

4: diethyl ether / 22 h / 20 °C

5: 91 percent / camphorsulfonic acid / methanol / 5 h

6: 94 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 18 h

7: 97 percent / oxalyl chloride, dimethyl sulfoxide, Et₃N / CH₂Cl₂ / 1 h / -78 °C

With dmap; dipyridinium dichromate; oxalyl dichloride; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1071/CH9901681

upstream raw materials:

methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2-deoxy-2-C-(2-methoxycarbonylethyl)-α-D-altropyranoside

methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-(3-hydroxypropyl)-α-D-altroside

methyl 4,6-O-benzylidene-2-deoxy-2-(2-propenyl)-α-D-allohexopyranoside

benzyl bromide

Downstream raw materials:

methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2,4-dideoxy-2-C-(2-methoxycarbonylethyl)-4-C-methyl-α-D-altro-and-ido-hexoside

methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2,4-dideoxy-2-C-(2-methoxycarbonylethyl)-4-C-methylene-α-D-arabino-hexoside