(4R,5R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3,3-dimethyl-5-triethylsilanyloxy-7-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-yl]-heptan-2-one

Base Information

Chemical Name:(4R,5R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3,3-dimethyl-5-triethylsilanyloxy-7-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-yl]-heptan-2-one
CAS No.:158574-41-5
Molecular Formula:C₅₃H₇₄O₈Si
Molecular Weight:867.251
Hs Code.:

(4R,5R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3,3-dimethyl-5-triethylsilanyloxy-7-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-yl]-heptan-2-one

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Chemical Property of (4R,5R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3,3-dimethyl-5-triethylsilanyloxy-7-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-yl]-heptan-2-one

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Technology Process of (4R,5R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3,3-dimethyl-5-triethylsilanyloxy-7-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-yl]-heptan-2-one

There total 13 articles about (4R,5R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3,3-dimethyl-5-triethylsilanyloxy-7-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-yl]-heptan-2-one 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:

: 2746-25-0
p-Methoxybenzyl bromide

: 158574-41-5
(4R,5R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3,3-dimethyl-5-triethylsilanyloxy-7-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-yl]-heptan-2-one

Guidance literature:: Multi-step reaction with 11 steps

1: 82 percent / (n-Bu)4NI, KH / tetrahydrofuran

3: 1.) TiCl₄ / 1.) CH₂Cl₂, 2.) CH₂Cl₂, -78 deg C

4: 1.) Me₄NHB(OAc)3, 2.) TsOH / 1.) MeCN, AcOH

5: W-2 Raney Ni / ethanol

6: Swern oxidation reagent

7: hexane; CH₂Cl₂ / -78 °C

8: 100 percent / camphorsulfonic acid / acetone / 25 °C

10: 1.) Et₃N, 4-dimethylaminopyridine, 2.) KH, <18>crown-6 / 2.) THF

With dmap; 18-crown-6 ether; Swern oxidation reagent; W-2 Raney Ni; camphor-10-sulfonic acid; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; potassium hydride; toluene-4-sulfonic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetone;

Reference yield:

: (4R,5S)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-hydroxy-3,3-dimethyl-dihydro-furan-2-one

: 158574-41-5
(4R,5R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3,3-dimethyl-5-triethylsilanyloxy-7-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-yl]-heptan-2-one

Guidance literature:: Multi-step reaction with 11 steps

1: 82 percent / (n-Bu)4NI, KH / tetrahydrofuran

3: 1.) TiCl₄ / 1.) CH₂Cl₂, 2.) CH₂Cl₂, -78 deg C

4: 1.) Me₄NHB(OAc)3, 2.) TsOH / 1.) MeCN, AcOH

5: W-2 Raney Ni / ethanol

6: Swern oxidation reagent

7: hexane; CH₂Cl₂ / -78 °C

8: 100 percent / camphorsulfonic acid / acetone / 25 °C

10: 1.) Et₃N, 4-dimethylaminopyridine, 2.) KH, <18>crown-6 / 2.) THF

With dmap; 18-crown-6 ether; Swern oxidation reagent; W-2 Raney Ni; camphor-10-sulfonic acid; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; potassium hydride; toluene-4-sulfonic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetone;

Reference yield:

: 158574-33-5
(R)-5-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3,3-dimethyl-furan-2,4-dione

: 158574-41-5
(4R,5R,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-3,3-dimethyl-5-triethylsilanyloxy-7-[(4S,5S,6R)-2,2,5-trimethyl-6-((R)-1-methyl-2-trityloxy-ethyl)-[1,3]dioxan-4-yl]-heptan-2-one

Guidance literature:: Multi-step reaction with 12 steps

1: 85 percent / KEt₃BH / tetrahydrofuran / -78 °C

2: 82 percent / (n-Bu)4NI, KH / tetrahydrofuran

4: 1.) TiCl₄ / 1.) CH₂Cl₂, 2.) CH₂Cl₂, -78 deg C

5: 1.) Me₄NHB(OAc)3, 2.) TsOH / 1.) MeCN, AcOH

6: W-2 Raney Ni / ethanol

7: Swern oxidation reagent

8: hexane; CH₂Cl₂ / -78 °C

9: 100 percent / camphorsulfonic acid / acetone / 25 °C

11: 1.) Et₃N, 4-dimethylaminopyridine, 2.) KH, <18>crown-6 / 2.) THF

With dmap; 18-crown-6 ether; KEt₃BH; Swern oxidation reagent; W-2 Raney Ni; camphor-10-sulfonic acid; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; potassium hydride; toluene-4-sulfonic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; ethanol; hexane; dichloromethane; acetone;