(4S,5S,6S,1R,2R)-4-benzyloxy-2-(tert-butyldimethylsilyloxy)-6-[(1'R,2'R)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-5-methoxymethyloxy-cyclohexancarboxylic acid

Base Information

• Chemical Name: (4S,5S,6S,1R,2R)-4-benzyloxy-2-(tert-butyldimethylsilyloxy)-6-[(1'R,2'R)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-5-methoxymethyloxy-cyclohexancarboxylic acid
• CAS No.: 905312-36-9
• Molecular Formula: C₃₂H₄₈O₁₀SSi
• Molecular Weight: 652.879
• Mol file: 905312-36-9.mol

Synonyms:(4S,5S,6S,1R,2R)-4-benzyloxy-2-(tert-butyldimethylsilyloxy)-6-[(1'R,2'R)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-5-methoxymethyloxy-cyclohexancarboxylic acid

Chemical Property of (4S,5S,6S,1R,2R)-4-benzyloxy-2-(tert-butyldimethylsilyloxy)-6-[(1'R,2'R)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-5-methoxymethyloxy-cyclohexancarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S,6S,1R,2R)-4-benzyloxy-2-(tert-butyldimethylsilyloxy)-6-[(1'R,2'R)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-5-methoxymethyloxy-cyclohexancarboxylic acid

There total 8 articles about (4S,5S,6S,1R,2R)-4-benzyloxy-2-(tert-butyldimethylsilyloxy)-6-[(1'R,2'R)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-5-methoxymethyloxy-cyclohexancarboxylic acid 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:

(1R,2R,3S,4S,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-[(1R,2R)-2-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyloxy)-propyl]-3-methoxymethoxy-cyclohexanecarboxylic acid (905312-35-8) → (4S,5S,6S,1R,2R)-4-benzyloxy-2-(tert-butyldimethylsilyloxy)-6-[(1'R,2'R)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-5-methoxymethyloxy-cyclohexancarboxylic acid (905312-36-9)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 - 20 ℃; for 0.333333h;

DOI:10.1016/j.tet.2006.04.079

Reference yield:

(4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone (581060-33-5) → (4S,5S,6S,1R,2R)-4-benzyloxy-2-(tert-butyldimethylsilyloxy)-6-[(1'R,2'R)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-5-methoxymethyloxy-cyclohexancarboxylic acid (905312-36-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: copper(I) cyanide / diethyl ether / -78 - 0 °C

1.2: diethyl ether / 0.5 h / -78 °C

1.3: 85 percent / diethyl ether / 0.33 h / -78 °C

2.1: 70 percent / Me₄NBH(OAc)3; acetic acid / tetrahydrofuran / 24 h / 0 - 20 °C

3.1: 100 percent / BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

4.1: 98 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 3.5 h / 50 °C

5.1: ozone / methanol / 0.08 h / -78 °C

5.2: Me₂S / methanol / 12 h / -78 - 20 °C

6.1: 6.1 mg / NaH₂PO₄*H₂O; HOSO₂NH₂; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

7.1: 3.9 mg / DDQ / CH₂Cl₂; H₂O / 0.33 h / 0 - 20 °C

With sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; amidosulfuric acid fluoride; copper(l) cyanide; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane; tert-butyl alcohol;

DOI:10.1016/j.tet.2006.04.079

Reference yield:

(2S,4R)-2-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-hydroxy-cyclohexan-1-one (581060-36-8) → (4S,5S,6S,1R,2R)-4-benzyloxy-2-(tert-butyldimethylsilyloxy)-6-[(1'R,2'R)-2'-hydroxy-1'-(p-toluenesulfonyloxy)propyl]-5-methoxymethyloxy-cyclohexancarboxylic acid (905312-36-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: MsCl; Et₃N / CH₂Cl₂ / 2.5 h / 0 °C

1.2: 3.50 g / HCl / H₂O

2.1: copper(I) cyanide / diethyl ether / -78 - 0 °C

2.2: diethyl ether / 0.5 h / -78 °C

2.3: 85 percent / diethyl ether / 0.33 h / -78 °C

3.1: 70 percent / Me₄NBH(OAc)3; acetic acid / tetrahydrofuran / 24 h / 0 - 20 °C

4.1: 100 percent / BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

5.1: 98 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 3.5 h / 50 °C

6.1: ozone / methanol / 0.08 h / -78 °C

6.2: Me₂S / methanol / 12 h / -78 - 20 °C

7.1: 6.1 mg / NaH₂PO₄*H₂O; HOSO₂NH₂; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

8.1: 3.9 mg / DDQ / CH₂Cl₂; H₂O / 0.33 h / 0 - 20 °C

With sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; amidosulfuric acid fluoride; copper(l) cyanide; ozone; acetic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane; tert-butyl alcohol;

DOI:10.1016/j.tet.2006.04.079

upstream raw materials:

(1R,2R,3S,4S,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-[(1R,2R)-2-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyloxy)-propyl]-3-methoxymethoxy-cyclohexanecarboxylic acid

(4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone

(2S,4R)-2-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-hydroxy-cyclohexan-1-one

(2S,3R,4R,6S)-6-benzyloxy-4-(tert-butyldimethylsilyloxy)-2-[(1'R,2'R)-1'-hydroxy-2'-(4-methoxybenzyloxy)propyl]-3-vinylcyclohexan-1-one