(6R,7R,10R,11R,14R,15S)-1-tert-butyldiphenylsilyloxy-15-(methoxymethoxy)-7,10:11,14-bisoxidoheptacos-3-yn-6-ol

Base Information

Chemical Name:(6R,7R,10R,11R,14R,15S)-1-tert-butyldiphenylsilyloxy-15-(methoxymethoxy)-7,10:11,14-bisoxidoheptacos-3-yn-6-ol
CAS No.:248601-81-2
Molecular Formula:C₄₅H₇₀O₆Si
Molecular Weight:735.133
Hs Code.:

Synonyms:(6R,7R,10R,11R,14R,15S)-1-tert-butyldiphenylsilyloxy-15-(methoxymethoxy)-7,10:11,14-bisoxidoheptacos-3-yn-6-ol

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Chemical Property of (6R,7R,10R,11R,14R,15S)-1-tert-butyldiphenylsilyloxy-15-(methoxymethoxy)-7,10:11,14-bisoxidoheptacos-3-yn-6-ol

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Technology Process of (6R,7R,10R,11R,14R,15S)-1-tert-butyldiphenylsilyloxy-15-(methoxymethoxy)-7,10:11,14-bisoxidoheptacos-3-yn-6-ol

There total 17 articles about (6R,7R,10R,11R,14R,15S)-1-tert-butyldiphenylsilyloxy-15-(methoxymethoxy)-7,10:11,14-bisoxidoheptacos-3-yn-6-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: 85.0%

: 88158-68-3
4-(tert-butyldiphenylsilyloxy)-1-butyne

: 248601-80-1
(2R,3R,6R,7R,10R,11S)-11-(methoxymethoxy)-1,2:3,6:7,10-trisoxidotricosane

: 248601-81-2
(6R,7R,10R,11R,14R,15S)-1-tert-butyldiphenylsilyloxy-15-(methoxymethoxy)-7,10:11,14-bisoxidoheptacos-3-yn-6-ol

Guidance literature:: 4-(tert-butyldiphenylsilyloxy)-1-butyne; With n-butyllithium; In tetrahydrofuran; at -78 - 20 ℃; for 1h;

(2R,3R,6R,7R,10R,11S)-11-(methoxymethoxy)-1,2:3,6:7,10-trisoxidotricosane; With boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1021/jo990599p

Reference yield:

: 142925-91-5
(4S,5S)-(-)-4,5-Dihydroxy-4,5-O-isopropylidenheptadecansaeure-methylester

: 248601-81-2
(6R,7R,10R,11R,14R,15S)-1-tert-butyldiphenylsilyloxy-15-(methoxymethoxy)-7,10:11,14-bisoxidoheptacos-3-yn-6-ol

Guidance literature:: Multi-step reaction with 17 steps

1.1: 97 percent / LiAlH₄ / diethyl ether / 0 °C / Heating

2.1: 84 percent / PCC; Celite / CH₂Cl₂ / 2 h / 20 °C

3.1: 88 percent / tetrahydrofuran; diethyl ether / 0.5 h / -20 °C

4.1: 86 percent / propionic acid / xylene / 2 h / Heating

5.1: 85 percent / TsOH / methanol; H₂O / 16 h / 20 °C

6.1: triethyl orthoacetate; chlorotrimethylsilane / CH₂Cl₂ / 0.5 h / 40 °C

6.2: 3.1 g / K₂CO₃ / methanol / 2 h / 20 °C

7.1: AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 16 h / 0 °C

7.2: 64 percent / Amberlyst 15 / CH₂Cl₂ / 16 h / 20 °C

8.1: 89 percent / diisopropylethylamine / CH₂Cl₂ / 16 h / 20 °C

9.1: 90 percent / DIBAL-H / tetrahydrofuran; toluene / 1 h / -78 °C

10.1: 84 percent / toluene / 16 h / 80 °C

11.1: 98 percent / DIBAL-H / tetrahydrofuran; toluene / 1 h / -78 °C

12.1: (+)-diethyl tartrate; Ti(i-PrO)4; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / -20 °C

12.2: 82 percent / TBHP / CH₂Cl₂; 2,2,4-trimethyl-pentane / 16 h / -20 °C

13.1: 96 percent / DMAP; diisopropylethylamine / CH₂Cl₂ / 16 h / 20 °C

14.1: 96 percent / triethylamine / CH₂Cl₂ / 2 h / -30 - 0 °C

15.1: 91 percent / TsOH / methanol / 2 h / 20 °C

16.1: 75 percent / K₂CO₃ / methanol / 1 h / 20 °C

17.1: n-BuLi / tetrahydrofuran / 1 h / -78 - 20 °C

17.2: 85 percent / BF₃*Et₂O / tetrahydrofuran / 1 h / -78 °C

With titanium(IV) isopropylate; dmap; lithium aluminium tetrahydride; n-butyllithium; chloro-trimethyl-silane; methanesulfonamide; 4 A molecular sieve; AD-mix-β; Celite; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; propionic acid; Triethyl orthoacetate; (+)-Weinsaeure-diethylester; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; toluene; xylene; tert-butyl alcohol; 1.1: Reduction / 2.1: Oxidation / 3.1: Grignard reaction / 4.1: Condensation / 5.1: Substitution / 6.1: Substitution / 6.2: Cyclization / 7.1: Sharpless asymmetric dihydroxylation / 7.2: Cyclization / 8.1: Substitution / 9.1: Reduction / 10.1: Wittig-Horner reaction / 11.1: Reduction / 12.1: Sharpless asymmetric epoxidation / 12.2: Cyclization / 13.1: Substitution / 14.1: Substitution / 15.1: Substitution / 16.1: Cyclization / 17.1: Metallation / 17.2: Condensation;
DOI:10.1021/jo990599p

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 248601-81-2
(6R,7R,10R,11R,14R,15S)-1-tert-butyldiphenylsilyloxy-15-(methoxymethoxy)-7,10:11,14-bisoxidoheptacos-3-yn-6-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 94 percent / DMAP; diisopropylethylamine / CH₂Cl₂ / 16 h / 20 °C

2.1: n-BuLi / tetrahydrofuran / 1 h / -78 - 20 °C

2.2: 85 percent / BF₃*Et₂O / tetrahydrofuran / 1 h / -78 °C

With dmap; n-butyllithium; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 1.1: Substitution / 2.1: Metallation / 2.2: Condensation;
DOI:10.1021/jo990599p