Acetic acid (1R,2S,4S)-2-acetoxy-5-benzyloxy-1-{(2R,3R,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-4-methoxy-pentyl ester

Base Information

• Chemical Name: Acetic acid (1R,2S,4S)-2-acetoxy-5-benzyloxy-1-{(2R,3R,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-4-methoxy-pentyl ester
• CAS No.: 357419-67-1
• Molecular Formula: C₄₁H₇₄O₁₁Si₂
• Molecular Weight: 799.203

Synonyms:Acetic acid (1R,2S,4S)-2-acetoxy-5-benzyloxy-1-{(2R,3R,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-4-methoxy-pentyl ester

Chemical Property of Acetic acid (1R,2S,4S)-2-acetoxy-5-benzyloxy-1-{(2R,3R,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-4-methoxy-pentyl ester

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Technology Process of Acetic acid (1R,2S,4S)-2-acetoxy-5-benzyloxy-1-{(2R,3R,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-4-methoxy-pentyl ester

There total 17 articles about Acetic acid (1R,2S,4S)-2-acetoxy-5-benzyloxy-1-{(2R,3R,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-4-methoxy-pentyl 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: 73.0%

acetic anhydride (108-24-7) + (S)-5-Benzyloxy-1-{(2R,3R,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-4-methoxy-pentane-1,2-diol → Acetic acid (S)-2-acetoxy-5-benzyloxy-1-{(2R,3R,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-4-methoxy-pentyl ester + Acetic acid (1R,2S,4S)-2-acetoxy-5-benzyloxy-1-{(2R,3R,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-4-methoxy-pentyl ester (357419-67-1)

Guidance literature:

With dmap; In pyridine; at 40 ℃; for 13h;

DOI:10.1002/chem.200600461

Reference yield:

(S)-benzyl glycidyl ether (2930-05-4,14618-80-5,89616-40-0,16495-13-9) → Acetic acid (1R,2S,4S)-2-acetoxy-5-benzyloxy-1-{(2R,3R,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-4-methoxy-pentyl ester (357419-67-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: nBuLi / hexane; tetrahydrofuran / 0.17 h

1.2: BF₃*OEt₂ / tetrahydrofuran; hexane / 2 h / -78 °C

2.1: lithium hexamethyldisilazide / tetrahydrofuran / 16 h / 40 °C

3.1: 8.8 g / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h

4.1: LiEt₃BH; Cp₂ZrCl₂ / tetrahydrofuran / 0.25 h

4.2: 88 percent / N-iodosuccinimide / tetrahydrofuran / 0.17 h

5.1: tBuLi / pentane; diethyl ether / 1.5 h / -78 °C

5.2: diethyl ether; pentane; toluene / 3.5 h

6.1: 1.58 g / pyridinium p-toluene sulfonate / CH₂Cl₂ / 0.5 h / 0 °C

7.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

8.1: [K₂OsO₂(OH)4]; N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; H₂O / 216 h / 0 - 10 °C

9.1: 73 percent / 4-N,N-dimethylaminopyridine / pyridine / 13 h / 40 °C

With 2,6-dimethylpyridine; dmap; potassium osmate; n-butyllithium; zirconocene dichloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; lithium triethylborohydride; 4-methylmorpholine N-oxide; lithium hexamethyldisilazane; In tetrahydrofuran; pyridine; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol; pentane;

DOI:10.1002/chem.200600461

Reference yield:

(2S)-1-O-benzyl-2-methoxypent-4-yn-1-ol (357419-50-2) → Acetic acid (1R,2S,4S)-2-acetoxy-5-benzyloxy-1-{(2R,3R,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl}-4-methoxy-pentyl ester (357419-67-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: LiEt₃BH; Cp₂ZrCl₂ / tetrahydrofuran / 0.25 h

1.2: 88 percent / N-iodosuccinimide / tetrahydrofuran / 0.17 h

2.1: tBuLi / pentane; diethyl ether / 1.5 h / -78 °C

2.2: diethyl ether; pentane; toluene / 3.5 h

3.1: 1.58 g / pyridinium p-toluene sulfonate / CH₂Cl₂ / 0.5 h / 0 °C

4.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / -78 °C

5.1: [K₂OsO₂(OH)4]; N-methylmorpholine-N-oxide / 2-methyl-propan-2-ol; H₂O / 216 h / 0 - 10 °C

6.1: 73 percent / 4-N,N-dimethylaminopyridine / pyridine / 13 h / 40 °C

With 2,6-dimethylpyridine; dmap; potassium osmate; zirconocene dichloride; tert.-butyl lithium; pyridinium p-toluenesulfonate; lithium triethylborohydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; water; tert-butyl alcohol; pentane;

DOI:10.1002/chem.200600461

upstream raw materials:

acetic anhydride

t-butyldimethylsiyl triflate

(S)-benzyl glycidyl ether

(R)-3-(tert-butyldimethylsilyloxy)-4-methoxybutanal

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