(4R,6R)-6-[(1R,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-butyl]-4-[(4R,6S)-6-((4S,6R)-6-bromomethyl-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Base Information

Chemical Name:(4R,6R)-6-[(1R,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-butyl]-4-[(4R,6S)-6-((4S,6R)-6-bromomethyl-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile
CAS No.:375827-03-5
Molecular Formula:C₄₀H₆₆BrNO₈Si
Molecular Weight:796.955
Hs Code.:

(4R,6R)-6-[(1R,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-butyl]-4-[(4R,6S)-6-((4S,6R)-6-bromomethyl-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Synonyms:(4R,6R)-6-[(1R,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-butyl]-4-[(4R,6S)-6-((4S,6R)-6-bromomethyl-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

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Chemical Property of (4R,6R)-6-[(1R,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-butyl]-4-[(4R,6S)-6-((4S,6R)-6-bromomethyl-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

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Technology Process of (4R,6R)-6-[(1R,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-butyl]-4-[(4R,6S)-6-((4S,6R)-6-bromomethyl-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

There total 15 articles about (4R,6R)-6-[(1R,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-butyl]-4-[(4R,6S)-6-((4S,6R)-6-bromomethyl-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile 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: 65.0%

: 375826-89-4
C₁₅H₂₆Br₂O₄

: 375826-90-7
(6R)-6-[(1R,2S)-4-benzyloxy-2-(tert-butyldimethylsilanyloxy)-1-methylbutyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

: 375827-03-5
(4R,6R)-6-[(1R,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-butyl]-4-[(4R,6S)-6-((4S,6R)-6-bromomethyl-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Guidance literature:: With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium diisopropyl amide; In tetrahydrofuran; at -78 - -50 ℃; for 1.41667h;
DOI:10.1016/S0040-4020(02)00666-X

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 375827-03-5
(4R,6R)-6-[(1R,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-butyl]-4-[(4R,6S)-6-((4S,6R)-6-bromomethyl-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Guidance literature:: Multi-step reaction with 8 steps

1.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

2.1: DIBAL-H / CH₂Cl₂ / 1.17 h / -78 °C

3.1: 1.29 g / SnCl₂ / CH₂Cl₂ / 18 h

4.1: NaBH₄ / methanol / 2 h / -50 °C

5.1: triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 3 h

6.1: DIBAL-H / CH₂Cl₂ / 1.5 h / -78 °C

7.1: KCN/18-crown-6 complex / CH₂Cl₂ / 12 h

7.2: 0.342 g / H₂O; dl-camphorsulfonic acid / acetone; CH₂Cl₂ / 18 h

8.1: 65 percent / DMPU; LDA / tetrahydrofuran / 1.42 h / -78 - -50 °C

With 2,6-dimethylpyridine; dmap; potassium cyanide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; 18-crown-6 ether; diisobutylaluminium hydride; triethylamine; tin(ll) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; 3.1: Roskamp homologation;
DOI:10.1016/S0040-4020(02)00666-X

Reference yield:

: 142929-76-8
(2S,3S)-5-Benzyloxy-3-hydroxy-2-methyl-pentanoic acid ethyl ester

: 375827-03-5
(4R,6R)-6-[(1R,2S)-4-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-butyl]-4-[(4R,6S)-6-((4S,6R)-6-bromomethyl-2,2-dimethyl-[1,3]dioxan-4-ylmethyl)-2,2-dimethyl-[1,3]dioxan-4-ylmethyl]-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Guidance literature:: Multi-step reaction with 8 steps

1.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

2.1: DIBAL-H / CH₂Cl₂ / 1.17 h / -78 °C

3.1: 1.29 g / SnCl₂ / CH₂Cl₂ / 18 h

4.1: NaBH₄ / methanol / 2 h / -50 °C

5.1: triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 3 h

6.1: DIBAL-H / CH₂Cl₂ / 1.5 h / -78 °C

7.1: KCN/18-crown-6 complex / CH₂Cl₂ / 12 h

7.2: 0.342 g / H₂O; dl-camphorsulfonic acid / acetone; CH₂Cl₂ / 18 h

8.1: 65 percent / DMPU; LDA / tetrahydrofuran / 1.42 h / -78 - -50 °C

With 2,6-dimethylpyridine; dmap; potassium cyanide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium tetrahydroborate; 18-crown-6 ether; diisobutylaluminium hydride; triethylamine; tin(ll) chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; 3.1: Roskamp homologation;
DOI:10.1016/S0040-4020(02)00666-X