(1S,2S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(1,2-dihydroxy-propyl)-1-(4-methoxy-benzyloxy)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester

Base Information

• Chemical Name: (1S,2S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(1,2-dihydroxy-propyl)-1-(4-methoxy-benzyloxy)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester
• CAS No.: 869102-88-5
• Molecular Formula: C₃₈H₅₀O₇Si
• Molecular Weight: 646.896
• Mol file: 869102-88-5.mol

Synonyms:

Chemical Property of (1S,2S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(1,2-dihydroxy-propyl)-1-(4-methoxy-benzyloxy)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(1,2-dihydroxy-propyl)-1-(4-methoxy-benzyloxy)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester

There total 3 articles about (1S,2S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(1,2-dihydroxy-propyl)-1-(4-methoxy-benzyloxy)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl 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:

(E)-(2S,3S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-3-methyl-2-((R)-2-methyl-4-trimethylsilanyl-but-3-ynyl)-hex-4-enoic acid methyl ester (869102-87-4) → (1S,2S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(1,2-dihydroxy-propyl)-1-(4-methoxy-benzyloxy)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester (869102-88-5)

Guidance literature:

Multi-step reaction with 3 steps

1: K₂CO₃ / methanol / 20 °C

2: 747 mg / second generation Grubbs' catalyst / toluene / 1 h / 80 °C

3: AD mix β; aq. MeSO2NH2 / 2-methyl-propan-2-ol

With methanesulfonamide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In methanol; toluene; tert-butyl alcohol; 3: Sharpless dihydroxylation;

DOI:10.1055/s-2005-872657

Reference yield:

(E)-(2S,3S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-3-methyl-2-((R)-2-methyl-but-3-ynyl)-hex-4-enoic acid methyl ester → (1S,2S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(1,2-dihydroxy-propyl)-1-(4-methoxy-benzyloxy)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester (869102-88-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 747 mg / second generation Grubbs' catalyst / toluene / 1 h / 80 °C

2: AD mix β; aq. MeSO2NH2 / 2-methyl-propan-2-ol

With methanesulfonamide; 1,4-bis(9-O-dihydroquinidine)phthalazine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; tert-butyl alcohol; 2: Sharpless dihydroxylation;

DOI:10.1055/s-2005-872657

Reference yield:

(E)-(2S,3S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-3-methyl-2-((R)-2-methyl-4-trimethylsilanyl-but-3-ynyl)-hex-4-enoic acid (1026570-55-7) → (1S,2S,5R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-4-(1,2-dihydroxy-propyl)-1-(4-methoxy-benzyloxy)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester (869102-88-5)

Guidance literature:

Multi-step reaction with 4 steps

1: K₂CO₃ / methanol / 20 °C

2: 747 mg / second generation Grubbs' catalyst / toluene / 1 h / 80 °C

3: AD mix β; aq. MeSO2NH2 / 2-methyl-propan-2-ol

With methanesulfonamide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In methanol; toluene; tert-butyl alcohol; 4: Sharpless dihydroxylation;

DOI:10.1055/s-2005-872657

upstream raw materials:

(E)-(2S,3S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-3-methyl-2-((R)-2-methyl-4-trimethylsilanyl-but-3-ynyl)-hex-4-enoic acid methyl ester

(E)-(2S,3S)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-2-(4-methoxy-benzyloxy)-3-methyl-2-((R)-2-methyl-4-trimethylsilanyl-but-3-ynyl)-hex-4-enoic acid

Downstream raw materials:

(1S,2S,5R)-2,4-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-1-hydroxy-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester

(1S,2S,5R)-2,4-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-1-(4-methoxy-benzyloxy)-2,5-dimethyl-cyclohex-3-enecarboxylic acid methyl ester