(2R,4R,5S,6R,7R)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-4-((E)-2-methoxymethoxy-vinyl)-2,6-dimethyl-nonane-1,5-diol

Base Information

Chemical Name:(2R,4R,5S,6R,7R)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-4-((E)-2-methoxymethoxy-vinyl)-2,6-dimethyl-nonane-1,5-diol
CAS No.:135799-72-3
Molecular Formula:C₂₈H₅₀O₆Si
Molecular Weight:510.787
Hs Code.:

Synonyms:(2R,4R,5S,6R,7R)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-4-((E)-2-methoxymethoxy-vinyl)-2,6-dimethyl-nonane-1,5-diol

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Chemical Property of (2R,4R,5S,6R,7R)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-4-((E)-2-methoxymethoxy-vinyl)-2,6-dimethyl-nonane-1,5-diol

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Technology Process of (2R,4R,5S,6R,7R)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-4-((E)-2-methoxymethoxy-vinyl)-2,6-dimethyl-nonane-1,5-diol

There total 12 articles about (2R,4R,5S,6R,7R)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-4-((E)-2-methoxymethoxy-vinyl)-2,6-dimethyl-nonane-1,5-diol 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: 78.0%

: (2R,4R,5S,6R,7R)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-1-tert-butylsilanyloxy-4-((E)-2-methoxymethoxy-vinyl)-2,6-dimethyl-nonan-5-ol

: 135799-72-3
(2R,4R,5S,6R,7R)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-4-((E)-2-methoxymethoxy-vinyl)-2,6-dimethyl-nonane-1,5-diol

Guidance literature:: With acetic acid; In tetrahydrofuran;
DOI:10.1021/jo00019a003

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 135799-72-3
(2R,4R,5S,6R,7R)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-4-((E)-2-methoxymethoxy-vinyl)-2,6-dimethyl-nonane-1,5-diol

Guidance literature:: Multi-step reaction with 7 steps

1: Et₃N

2: DIBAH / CH₂Cl₂

3: NaH / dimethylformamide

4: 95 percent / CH₂(CH₂SH)2, BF₃*Et₂O

5: 94 percent / Swern

6: 79 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

7: 78 percent / 70percent HOAc / tetrahydrofuran

With 1.3-propanedithiol; boron trifluoride diethyl etherate; sodium hydride; diisobutylaluminium hydride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00019a003

Reference yield:

: 135799-60-9,135799-76-7
(3R,4R)-4-Methyl-5-(tetrahydro-pyran-2-yloxy)-pentane-1,3-diol

: 135799-72-3
(2R,4R,5S,6R,7R)-9-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-4-((E)-2-methoxymethoxy-vinyl)-2,6-dimethyl-nonane-1,5-diol

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine

2: Et₃N

3: DIBAH / CH₂Cl₂

4: NaH / dimethylformamide

5: 95 percent / CH₂(CH₂SH)2, BF₃*Et₂O

6: 94 percent / Swern

7: 79 percent / BF₃*OEt₂ / CH₂Cl₂ / -78 °C

8: 78 percent / 70percent HOAc / tetrahydrofuran

With pyridine; 1.3-propanedithiol; boron trifluoride diethyl etherate; sodium hydride; diisobutylaluminium hydride; acetic acid; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00019a003