(R)-3-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propane-1,2-diol

Base Information

Chemical Name:(R)-3-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propane-1,2-diol
CAS No.:876911-63-6
Molecular Formula:C₃₃H₅₈O₆Si₂
Molecular Weight:606.991
Hs Code.:

(R)-3-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propane-1,2-diol

Synonyms:(R)-3-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propane-1,2-diol

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Chemical Property of (R)-3-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propane-1,2-diol

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Technology Process of (R)-3-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propane-1,2-diol

There total 11 articles about (R)-3-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propane-1,2-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%

: 876911-38-5
(2S,3S,5S)-2-(7-Benzyloxy-hept-2-ynyl)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-allyl]-tetrahydro-furan

: 876911-63-6
(R)-3-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propane-1,2-diol

Guidance literature:: With AD-mix-α; In water; tert-butyl alcohol; at 0 ℃; for 40h;
DOI:10.1021/jo051889a

Reference yield:

: 876911-27-2
((E)-10-Chloro-dec-8-en-5-ynyloxymethyl)-benzene

: 876911-63-6
(R)-3-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propane-1,2-diol

Guidance literature:: Multi-step reaction with 10 steps

1.1: CH₃MgCl / tetrahydrofuran / 3 h / 50 - 60 °C

1.2: 86 percent / CuCl / tetrahydrofuran / 3 h / Heating

2.1: 92 percent / PPTS / ethanol / 6 h / 55 °C

3.1: 60 percent / LiAlH₄ / tetrahydrofuran / 24 h / Heating

4.1: 72 percent / titanium(IV) isopropoxide; (-)-diethyl D-tartrate; tert-butyl hydroperoxide / CH₂Cl₂ / 15 h / -30 - -20 °C

5.1: 95 percent / DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

6.1: 92 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 40 h / 0 °C

7.1: 65 percent / K₂CO₃ / methanol / 4 h / 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -20 - -10 °C

8.2: 70 percent / tetrahydrofuran / -20 - 20 °C

9.1: 99 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

10.1: 78 percent / AD-mix-α / 2-methyl-propan-2-ol; H2O / 40 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; AD-mix-α; lithium aluminium tetrahydride; n-butyllithium; diethyl (2S,3S)-tartrate; methanesulfonamide; methylmagnesium chloride; pyridinium p-toluenesulfonate; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; tert-butyl alcohol; 4.1: Sharpless asymmetric epoxidation / 6.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo051889a

Reference yield:

: 876911-30-7
(2E,5E)-13-Benzyloxy-trideca-2,5-dien-8-yn-1-ol

: 876911-63-6
(R)-3-[(2S,4S,5S)-5-(7-Benzyloxy-hept-2-ynyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-3-(tert-butyl-dimethyl-silanyloxy)-propane-1,2-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 72 percent / titanium(IV) isopropoxide; (-)-diethyl D-tartrate; tert-butyl hydroperoxide / CH₂Cl₂ / 15 h / -30 - -20 °C

2.1: 95 percent / DMAP; Et₃N / CH₂Cl₂ / 0 - 20 °C

3.1: 92 percent / AD-mix-α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 40 h / 0 °C

4.1: 65 percent / K₂CO₃ / methanol / 4 h / 20 °C

5.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -20 - -10 °C

5.2: 70 percent / tetrahydrofuran / -20 - 20 °C

6.1: 99 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

7.1: 78 percent / AD-mix-α / 2-methyl-propan-2-ol; H2O / 40 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; AD-mix-α; n-butyllithium; diethyl (2S,3S)-tartrate; methanesulfonamide; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; water; tert-butyl alcohol; 1.1: Sharpless asymmetric epoxidation / 3.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo051889a