(Z)-(S)-1-[(4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-((4S,6R)-2,2-dimethyl-6-trityloxymethyl-[1,3]dioxan-4-yl)-prop-2-en-1-ol

Base Information

Chemical Name:(Z)-(S)-1-[(4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-((4S,6R)-2,2-dimethyl-6-trityloxymethyl-[1,3]dioxan-4-yl)-prop-2-en-1-ol
CAS No.:112031-57-9
Molecular Formula:C₅₂H₆₂O₇Si
Molecular Weight:827.146
Hs Code.:

(Z)-(S)-1-[(4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-((4S,6R)-2,2-dimethyl-6-trityloxymethyl-[1,3]dioxan-4-yl)-prop-2-en-1-ol

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Chemical Property of (Z)-(S)-1-[(4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-((4S,6R)-2,2-dimethyl-6-trityloxymethyl-[1,3]dioxan-4-yl)-prop-2-en-1-ol

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Technology Process of (Z)-(S)-1-[(4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-((4S,6R)-2,2-dimethyl-6-trityloxymethyl-[1,3]dioxan-4-yl)-prop-2-en-1-ol

There total 9 articles about (Z)-(S)-1-[(4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-((4S,6R)-2,2-dimethyl-6-trityloxymethyl-[1,3]dioxan-4-yl)-prop-2-en-1-ol 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:

: 112051-45-3
(4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxane-4-carboxylic acid methyl ester

: 112031-57-9
(Z)-(S)-1-[(4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-((4S,6R)-2,2-dimethyl-6-trityloxymethyl-[1,3]dioxan-4-yl)-prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1: DIBAL-H / toluene / -23 °C

2: DMAP / pyridine

3: nBu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran

4: 1.) (COCl)2, DMSO, 2.) Et₃N

5: 1.) Ph₃P, 2.) n-BuLi / 1.) CH₂Cl₂, -78 deg C, 2.) THF, -78 deg C

6: 1.) n-BuLi / 1.) THF, -78 deg C

7: Hydrogen / Lindlar-Pd / ethyl acetate

With dmap; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; pyridine; ethyl acetate; toluene;
DOI:10.1016/S0040-4039(00)95310-3

Reference yield:

: 102717-30-6
(3R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxy-dihydro-furan-2-one

: 112031-57-9
(Z)-(S)-1-[(4R,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-3-((4S,6R)-2,2-dimethyl-6-trityloxymethyl-[1,3]dioxan-4-yl)-prop-2-en-1-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) aq. LiOH / 1.) THF

2: CSA

3: DIBAL-H / toluene / -23 °C

4: DMAP / pyridine

5: nBu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran

6: 1.) (COCl)2, DMSO, 2.) Et₃N

7: 1.) Ph₃P, 2.) n-BuLi / 1.) CH₂Cl₂, -78 deg C, 2.) THF, -78 deg C

8: 1.) n-BuLi / 1.) THF, -78 deg C

9: Hydrogen / Lindlar-Pd / ethyl acetate

With dmap; lithium hydroxide; n-butyllithium; oxalyl dichloride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; Lindlar's catalyst; In tetrahydrofuran; pyridine; ethyl acetate; toluene;
DOI:10.1016/S0040-4039(00)95310-3