2-(trimethylsilyl)ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

Base Information

Chemical Name:2-(trimethylsilyl)ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside
CAS No.:117253-07-3
Molecular Formula:C₃₅H₄₁NO₈Si
Molecular Weight:631.798
Hs Code.:

Synonyms:2-(trimethylsilyl)ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

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Chemical Property of 2-(trimethylsilyl)ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

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Technology Process of 2-(trimethylsilyl)ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

There total 8 articles about 2-(trimethylsilyl)ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside 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: 91.0%

: 3396-11-0
cesium acetate

: 117253-06-2
2-(trimethylsilyl)ethyl 4-O-(phenylsulfonyl)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

: 117253-07-3
2-(trimethylsilyl)ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

Guidance literature:: With 3 A molecular sieve; In N,N-dimethyl-formamide; at 130 ℃; for 3.5h;
DOI:10.1021/jo00259a006

Reference yield:

: 187022-30-6
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-α/β-D-glucopyranosyl chloride

: 117253-07-3
2-(trimethylsilyl)ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1: 64 percent / Hg(CN)2 / 1,2-dichloro-ethane / 1.) 70 deg C, 4 h, 2.) 50 deg C, 16 h

2: 96 percent / MeONa / methanol / 2.5 h / 22 °C

3: 91 percent / p-TsOH*H₂O / acetonitrile / 0.75 h

4: 1.) NaH / 1.) DMF, 2.) DMF, 22 deg C, 3 h

5: 86 percent / etheral HCl, NaCNBH₃, molecular sieves 3A / tetrahydrofuran / 1 h / 0 °C

6: 60 percent / pyridine, 4-(dimethylamino)pyridine / 24 h / 90 °C

7: 91 percent / molecular sieves 3A / dimethylformamide / 3.5 h / 130 °C

With pyridine; hydrogenchloride; dmap; 3 A molecular sieve; sodium methylate; mercury(II) cyanide; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00259a006

Reference yield:

: 10022-13-6,31505-44-9,81704-02-1,116347-84-3,131234-07-6,144300-04-9,79733-86-1
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

: 117253-07-3
2-(trimethylsilyl)ethyl 4-O-acetyl-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / ZnCl2, α,α-dichloromethyl methyl ether / CH2Cl2 / 2 h / 22 °C

2: 64 percent / Hg(CN)2 / 1,2-dichloro-ethane / 1.) 70 deg C, 4 h, 2.) 50 deg C, 16 h

3: 96 percent / MeONa / methanol / 2.5 h / 22 °C

4: 91 percent / p-TsOH*H₂O / acetonitrile / 0.75 h

5: 1.) NaH / 1.) DMF, 2.) DMF, 22 deg C, 3 h

6: 86 percent / etheral HCl, NaCNBH₃, molecular sieves 3A / tetrahydrofuran / 1 h / 0 °C

7: 60 percent / pyridine, 4-(dimethylamino)pyridine / 24 h / 90 °C

8: 91 percent / molecular sieves 3A / dimethylformamide / 3.5 h / 130 °C

With pyridine; hydrogenchloride; dmap; Dichloromethyl methyl ether; 3 A molecular sieve; sodium methylate; mercury(II) cyanide; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; zinc(II) chloride; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00259a006