(2R,3aR,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-phenyl)-4-[(R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-triethylsilanyl-3-triethylsilanyloxy-hexa-1,5-diynyl]-3a-hydroxymethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

Base Information

Chemical Name:(2R,3aR,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-phenyl)-4-[(R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-triethylsilanyl-3-triethylsilanyloxy-hexa-1,5-diynyl]-3a-hydroxymethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol
CAS No.:189105-20-2
Molecular Formula:C₄₄H₇₄O₁₀Si₃
Molecular Weight:847.322
Hs Code.:

(2R,3aR,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-phenyl)-4-[(R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-triethylsilanyl-3-triethylsilanyloxy-hexa-1,5-diynyl]-3a-hydroxymethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

Synonyms:(2R,3aR,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-phenyl)-4-[(R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-triethylsilanyl-3-triethylsilanyloxy-hexa-1,5-diynyl]-3a-hydroxymethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

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Chemical Property of (2R,3aR,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-phenyl)-4-[(R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-triethylsilanyl-3-triethylsilanyloxy-hexa-1,5-diynyl]-3a-hydroxymethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

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Technology Process of (2R,3aR,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-phenyl)-4-[(R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-triethylsilanyl-3-triethylsilanyloxy-hexa-1,5-diynyl]-3a-hydroxymethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

There total 6 articles about (2R,3aR,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-phenyl)-4-[(R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-triethylsilanyl-3-triethylsilanyloxy-hexa-1,5-diynyl]-3a-hydroxymethyl-tetrahydro-cyclopenta[1,3]dioxol-4-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: 84.0%

: (R)-4-((R)-1-Ethynyl-4-triethylsilanyl-1-triethylsilanyloxy-but-3-ynyl)-2,2-dimethyl-[1,3]dioxolane

: 189105-14-4
(2R,3aR,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-phenyl)-3a-hydroxymethyl-tetrahydro-cyclopenta[1,3]dioxol-4-one

: 189105-20-2
(2R,3aR,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-phenyl)-4-[(R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-triethylsilanyl-3-triethylsilanyloxy-hexa-1,5-diynyl]-3a-hydroxymethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

Guidance literature:: With n-butyllithium; cerium(III) chloride; In tetrahydrofuran; at -78 ℃;
DOI:10.1055/s-1997-780

Reference yield:

: (S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-iodo-cyclopent-2-enol

: 189105-20-2
(2R,3aR,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-phenyl)-4-[(R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-triethylsilanyl-3-triethylsilanyloxy-hexa-1,5-diynyl]-3a-hydroxymethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) Et₃N, PdCl₂(PPh₃)2, 2.) DIBAL, 3.) pyridine / 1.) MeOH, 60 deg C, 2.) CH₂Cl₂, -78 deg C

2: 87 percent / OsO₄, MNO / acetone; H₂O

3: 1.) TsOH, 2.) K₂CO₃ / 1.) benzene, reflux, 30 min, 2.) MeOH

4: 1.) Bu₂SnO, 2.) NBS / 2.) toluene, reflux,, 2.) CHCl₃

5: 84 percent / BuLi, CeCl₃ / tetrahydrofuran / -78 °C

With pyridine; bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; osmium(VIII) oxide; n-butyllithium; cerium(III) chloride; manganese(II) oxide; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; water; acetone;
DOI:10.1055/s-1997-780

Reference yield:

: (S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-iodo-cyclopent-2-enone

: 189105-20-2
(2R,3aR,6S,6aR)-6-(tert-Butyl-dimethyl-silanyloxy)-2-(3,4-dimethoxy-phenyl)-4-[(R)-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-triethylsilanyl-3-triethylsilanyloxy-hexa-1,5-diynyl]-3a-hydroxymethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 94 percent / NaBH₄, CeCl₃*7H₂O / methanol / -78 °C

2: 1.) Et₃N, PdCl₂(PPh₃)2, 2.) DIBAL, 3.) pyridine / 1.) MeOH, 60 deg C, 2.) CH₂Cl₂, -78 deg C

3: 87 percent / OsO₄, MNO / acetone; H₂O

4: 1.) TsOH, 2.) K₂CO₃ / 1.) benzene, reflux, 30 min, 2.) MeOH

5: 1.) Bu₂SnO, 2.) NBS / 2.) toluene, reflux,, 2.) CHCl₃

6: 84 percent / BuLi, CeCl₃ / tetrahydrofuran / -78 °C

With pyridine; bis-triphenylphosphine-palladium(II) chloride; sodium tetrahydroborate; N-Bromosuccinimide; osmium(VIII) oxide; n-butyllithium; cerium(III) chloride; manganese(II) oxide; diisobutylaluminium hydride; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; water; acetone;
DOI:10.1055/s-1997-780