{(3S,4S)-4-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methylsulfanylmethoxy-oct-6-ynyloxy}-tert-butyl-diphenyl-silane

Base Information

• Chemical Name: {(3S,4S)-4-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methylsulfanylmethoxy-oct-6-ynyloxy}-tert-butyl-diphenyl-silane
• CAS No.: 549505-03-5
• Molecular Formula: C₄₄H₅₄O₆SSi
• Molecular Weight: 739.061

Synonyms:{(3S,4S)-4-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methylsulfanylmethoxy-oct-6-ynyloxy}-tert-butyl-diphenyl-silane

Chemical Property of {(3S,4S)-4-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methylsulfanylmethoxy-oct-6-ynyloxy}-tert-butyl-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(3S,4S)-4-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methylsulfanylmethoxy-oct-6-ynyloxy}-tert-butyl-diphenyl-silane

There total 13 articles about {(3S,4S)-4-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methylsulfanylmethoxy-oct-6-ynyloxy}-tert-butyl-diphenyl-silane 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: 99.0%

Methanesulfonic acid (1R,6S,7S)-6-benzyloxy-9-(tert-butyl-diphenyl-silanyloxy)-1-[(R)-1-hydroxy-2-(4-methoxy-benzyloxy)-ethyl]-7-methylsulfanylmethoxy-non-3-ynyl ester (549505-14-8) → {(3S,4S)-4-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methylsulfanylmethoxy-oct-6-ynyloxy}-tert-butyl-diphenyl-silane (549505-03-5)

Guidance literature:

With potassium carbonate; In methanol; dichloromethane;

DOI:10.1016/S0040-4039(03)00432-5

Reference yield:

5-tert-butyldimethylsilyl ether of (4S,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one (106183-57-7) → {(3S,4S)-4-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methylsulfanylmethoxy-oct-6-ynyloxy}-tert-butyl-diphenyl-silane (549505-03-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 81 percent / Ac₂O / acetic acid / 70 °C

2: 87 percent / LiBH₄ / diethyl ether

3: imidazole / dimethylformamide

4: pyridine; DMAP / CH₂Cl₂

5: 78 percent / 1N HCl / methanol; tetrahydrofuran

6: 86 percent / K₂CO₃ / methanol; CH₂Cl₂

7: 51 percent / dimethylsulfoxide; tetrahydrofuran

8: 97 percent / NaH; Bu₄NI / tetrahydrofuran

9: 80 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

10: 98 percent / TEA; DMAP / CH₂Cl₂

11: 98 percent / 80 percent aq. AcOH / tetrahydrofuran

12: 99 percent / K₂CO₃ / methanol; CH₂Cl₂

With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium borohydride; n-butyllithium; TEA; boron trifluoride diethyl etherate; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; acetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; 9: Yamaguchi method;

DOI:10.1016/S0040-4039(03)00432-5

Reference yield:

2-deoxy-D-ribonolactone (34371-14-7) → {(3S,4S)-4-Benzyloxy-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-3-methylsulfanylmethoxy-oct-6-ynyloxy}-tert-butyl-diphenyl-silane (549505-03-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 70 percent / AgNO₃; pyridine / acetonitrile

2: 81 percent / Ac₂O / acetic acid / 70 °C

3: 87 percent / LiBH₄ / diethyl ether

4: imidazole / dimethylformamide

5: pyridine; DMAP / CH₂Cl₂

6: 78 percent / 1N HCl / methanol; tetrahydrofuran

7: 86 percent / K₂CO₃ / methanol; CH₂Cl₂

8: 51 percent / dimethylsulfoxide; tetrahydrofuran

9: 97 percent / NaH; Bu₄NI / tetrahydrofuran

10: 80 percent / n-BuLi; BF₃*OEt₂ / tetrahydrofuran / -78 °C

11: 98 percent / TEA; DMAP / CH₂Cl₂

12: 98 percent / 80 percent aq. AcOH / tetrahydrofuran

13: 99 percent / K₂CO₃ / methanol; CH₂Cl₂

With pyridine; 1H-imidazole; hydrogenchloride; dmap; lithium borohydride; n-butyllithium; TEA; boron trifluoride diethyl etherate; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; silver nitrate; acetic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 10: Yamaguchi method;

DOI:10.1016/S0040-4039(03)00432-5

upstream raw materials:

Methanesulfonic acid (1R,6S,7S)-6-benzyloxy-9-(tert-butyl-diphenyl-silanyloxy)-1-[(R)-1-hydroxy-2-(4-methoxy-benzyloxy)-ethyl]-7-methylsulfanylmethoxy-non-3-ynyl ester

5-tert-butyldimethylsilyl ether of (4S,5R)-4-hydroxy-5-hydroxymethyltetrahydrofuran-2-one

2-deoxy-D-ribonolactone

(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-methylsulfanylmethoxy-dihydro-furan-2-one

Downstream raw materials:

(Z)-(3S,4S)-4-Benzyloxy-1-(tert-butyl-diphenyl-silanyloxy)-8-[(2S,3R)-3-(4-methoxy-benzyloxymethyl)-oxiranyl]-oct-6-en-3-ol

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