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

Base Information

• Chemical Name: 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
• CAS No.: 549505-14-8
• Molecular Formula: C₄₅H₅₈O₉S₂Si
• Molecular Weight: 835.168

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of 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

There total 12 articles about 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 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: 98.0%

Methanesulfonic acid (1R,6S,7S)-6-benzyloxy-9-(tert-butyl-diphenyl-silanyloxy)-1-[(R)-2-(4-methoxy-benzyloxy)-1-triethylsilanyloxy-ethyl]-7-methylsulfanylmethoxy-non-3-ynyl ester (549505-13-7) → 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)

Guidance literature:

With acetic acid; In tetrahydrofuran;

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) → 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)

Guidance literature:

Multi-step reaction with 11 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

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) → 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)

Guidance literature:

Multi-step reaction with 12 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

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)-2-(4-methoxy-benzyloxy)-1-triethylsilanyloxy-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:

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

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