[(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((E)-3-{(S)-6-[(2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-yl]-methanol

Base Information

Chemical Name:[(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((E)-3-{(S)-6-[(2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-yl]-methanol
CAS No.:247146-85-6
Molecular Formula:C₄₀H₇₀O₇Si₂
Molecular Weight:719.163
Hs Code.:

[(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((E)-3-{(S)-6-[(2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-yl]-methanol

Synonyms:[(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((E)-3-{(S)-6-[(2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-yl]-methanol

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Chemical Property of [(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((E)-3-{(S)-6-[(2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-yl]-methanol

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Technology Process of [(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((E)-3-{(S)-6-[(2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-yl]-methanol

There total 35 articles about [(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((E)-3-{(S)-6-[(2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-yl]-methanol 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: 75.0%

: 215876-20-3
6-{3-[4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yl]-1,1-dimethyl-allyl}-2-[2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-3,4-dihydro-2H-pyran

: 247146-85-6
[(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((E)-3-{(S)-6-[(2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -15 ℃;
DOI:10.1021/ja990860j

Reference yield:

: 215876-11-2
(2R,4S,6S)-2-Benzyloxymethyl-6-hydroxymethyl-tetrahydro-pyran-4-ol

: 247146-85-6
[(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((E)-3-{(S)-6-[(2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 7 steps

1.1: imidazole; DMAP / CH₂Cl₂

2.1: H₂; AcOH / 10 percent Pd/C / ethyl acetate / 760 Torr

3.1: 85 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -50 °C

4.1: n-BuLi / tetrahydrofuran / -78 °C

4.2: tetrahydrofuran / -78 - -50 °C

5.1: DMAP / CH₂Cl₂

6.1: 64 percent / Mg; HgCl₂; EtOH

7.1: 75 percent / TBAF / tetrahydrofuran / -15 °C

With 1H-imidazole; dmap; n-butyllithium; oxalyl dichloride; ethanol; tetrabutyl ammonium fluoride; hydrogen; magnesium; acetic acid; dimethyl sulfoxide; triethylamine; mercury dichloride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; 1.1: silylation / 2.1: Hydrogenolysis / 3.1: Oxidation / 4.1: Metallation / 4.2: Substitution / 5.1: Acetylation / 6.1: Deacetylation / 7.1: desilylation;
DOI:10.1021/ja990860j

Reference yield:

: 247146-46-9
2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran

: 247146-85-6
[(2S,4R,6R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-((E)-3-{(S)-6-[(2R,3R)-2-(tert-butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-tetrahydro-pyran-2-yl]-methanol

Guidance literature:: Multi-step reaction with 6 steps

1.1: H₂; AcOH / 10 percent Pd/C / ethyl acetate / 760 Torr

2.1: 85 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - -50 °C

3.1: n-BuLi / tetrahydrofuran / -78 °C

3.2: tetrahydrofuran / -78 - -50 °C

4.1: DMAP / CH₂Cl₂

5.1: 64 percent / Mg; HgCl₂; EtOH

6.1: 75 percent / TBAF / tetrahydrofuran / -15 °C

With dmap; n-butyllithium; oxalyl dichloride; ethanol; tetrabutyl ammonium fluoride; hydrogen; magnesium; acetic acid; dimethyl sulfoxide; triethylamine; mercury dichloride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; 1.1: Hydrogenolysis / 2.1: Oxidation / 3.1: Metallation / 3.2: Substitution / 4.1: Acetylation / 5.1: Deacetylation / 6.1: desilylation;
DOI:10.1021/ja990860j