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

Base Information

Chemical Name:methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2,4-dideoxy-2-C-(2-methoxycarbonylethyl)-4-C-methylene-α-D-arabino-hexoside
CAS No.:131529-56-1
Molecular Formula:C₂₅H₄₀O₆Si
Molecular Weight:464.674
Hs Code.:

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

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

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

There total 10 articles about methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2,4-dideoxy-2-C-(2-methoxycarbonylethyl)-4-C-methylene-α-D-arabino-hexoside 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:

: 126108-10-9
methyl 4,6-O-benzylidene-2-deoxy-2-(2-propenyl)-α-D-allohexopyranoside

: 131529-56-1
methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2,4-dideoxy-2-C-(2-methoxycarbonylethyl)-4-C-methylene-α-D-arabino-hexoside

Guidance literature:: Multi-step reaction with 8 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

8: 1.) t-BuOK / 1.) toluene, 30 min, 2.) 70 deg C, 29 h

With dmap; dipyridinium dichromate; oxalyl dichloride; camphor-10-sulfonic acid; potassium tert-butylate; 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:

: 100-39-0
benzyl bromide

: 131529-56-1
methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2,4-dideoxy-2-C-(2-methoxycarbonylethyl)-4-C-methylene-α-D-arabino-hexoside

Guidance literature:: Multi-step reaction with 8 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

8: 1.) t-BuOK / 1.) toluene, 30 min, 2.) 70 deg C, 29 h

With dmap; dipyridinium dichromate; oxalyl dichloride; camphor-10-sulfonic acid; potassium tert-butylate; 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:

: 131529-43-6
methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-C-(prop-2-enyl)-α-D-altropyranoside

: 131529-56-1
methyl 3-O-benzyl-6-O-t-butyldimethylsilyl-2,4-dideoxy-2-C-(2-methoxycarbonylethyl)-4-C-methylene-α-D-arabino-hexoside

Guidance literature:: Multi-step reaction with 7 steps

2: 6.1 g / pyridinium dichromate / dimethylformamide / 22 h

3: diethyl ether / 22 h / 20 °C

4: 91 percent / camphorsulfonic acid / methanol / 5 h

5: 94 percent / Et₃N, 4-dimethylaminopyridine / CH₂Cl₂ / 18 h

6: 97 percent / oxalyl chloride, dimethyl sulfoxide, Et₃N / CH₂Cl₂ / 1 h / -78 °C

7: 1.) t-BuOK / 1.) toluene, 30 min, 2.) 70 deg C, 29 h

With dmap; dipyridinium dichromate; oxalyl dichloride; camphor-10-sulfonic acid; potassium tert-butylate; dimethyl sulfoxide; triethylamine; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1071/CH9901681