(2R,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-4-{(2R,3R)-3-[(1R,2R)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-triisopropylsilanyloxy-butyl]-oxiranyl}-3-(4-methoxy-benzyloxy)-butan-2-ol

Base Information

• Chemical Name: (2R,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-4-{(2R,3R)-3-[(1R,2R)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-triisopropylsilanyloxy-butyl]-oxiranyl}-3-(4-methoxy-benzyloxy)-butan-2-ol
• CAS No.: 500103-08-2
• Molecular Formula: C₄₀H₇₈O₇Si₃
• Molecular Weight: 755.312

Synonyms:(2R,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-4-{(2R,3R)-3-[(1R,2R)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-triisopropylsilanyloxy-butyl]-oxiranyl}-3-(4-methoxy-benzyloxy)-butan-2-ol

Chemical Property of (2R,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-4-{(2R,3R)-3-[(1R,2R)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-triisopropylsilanyloxy-butyl]-oxiranyl}-3-(4-methoxy-benzyloxy)-butan-2-ol

Chemical Property:

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Technology Process of (2R,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-4-{(2R,3R)-3-[(1R,2R)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-triisopropylsilanyloxy-butyl]-oxiranyl}-3-(4-methoxy-benzyloxy)-butan-2-ol

There total 17 articles about (2R,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-4-{(2R,3R)-3-[(1R,2R)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-triisopropylsilanyloxy-butyl]-oxiranyl}-3-(4-methoxy-benzyloxy)-butan-2-ol 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:

(2R,3S)-2-Hydroxy-3-phenylsulfanylcarbonyl-butyric acid ethyl ester (246510-31-6) → (2R,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-4-{(2R,3R)-3-[(1R,2R)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-triisopropylsilanyloxy-butyl]-oxiranyl}-3-(4-methoxy-benzyloxy)-butan-2-ol (500103-08-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 98 percent / imidazole; 4-(N,N-dimethylamino)pyridine / dimethylformamide / 0 °C

2.1: 95 percent / Et₃SiH / Pd/C / acetone

3.1: 84 percent / Zn; [(cyclopentadienyl)2ZrCl₂] / tetrahydrofuran / 0 °C

4.1: [(Ph₃P)3RhCl] / tetrahydrofuran / 0 °C

5.1: H₂O₂ / ethanol / pH 7

6.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

7.1: 89 percent / DIBAL-H / toluene / -78 °C

8.1: lithium hexamethyldisilazide / tetrahydrofuran / -78 °C

8.2: 79 percent / tetrahydrofuran / -78 - 0 °C

9.1: 87 percent / K₂CO₃ / methanol; CH₂Cl₂

10.1: 95 percent / meta-chloroperoxybenzoic acid / CH₂Cl₂ / 0 °C

11.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

12.1: 79 percent / lithium di-tert-butylbiphenylide / tetrahydrofuran / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; triethylsilane; dmap; Wilkinson's catalyst; zirconocene dichloride; lithium di-tert-butylbiphenylide; dihydrogen peroxide; diisobutylaluminium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 8.2: Wittig coupling;

DOI:10.1002/1521-3773(20021202)41:23<4560::AID-ANIE4560>3.0.CO;2-B

Reference yield:

(2R,3S)-3-Phenylsulfanylcarbonyl-2-triphenylsilanyloxy-butyric acid ethyl ester (500103-02-6) → (2R,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-4-{(2R,3R)-3-[(1R,2R)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-triisopropylsilanyloxy-butyl]-oxiranyl}-3-(4-methoxy-benzyloxy)-butan-2-ol (500103-08-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 95 percent / Et₃SiH / Pd/C / acetone

2.1: 84 percent / Zn; [(cyclopentadienyl)2ZrCl₂] / tetrahydrofuran / 0 °C

3.1: [(Ph₃P)3RhCl] / tetrahydrofuran / 0 °C

4.1: H₂O₂ / ethanol / pH 7

5.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

6.1: 89 percent / DIBAL-H / toluene / -78 °C

7.1: lithium hexamethyldisilazide / tetrahydrofuran / -78 °C

7.2: 79 percent / tetrahydrofuran / -78 - 0 °C

8.1: 87 percent / K₂CO₃ / methanol; CH₂Cl₂

9.1: 95 percent / meta-chloroperoxybenzoic acid / CH₂Cl₂ / 0 °C

10.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

11.1: 79 percent / lithium di-tert-butylbiphenylide / tetrahydrofuran / -78 °C

With 2,6-dimethylpyridine; triethylsilane; Wilkinson's catalyst; zirconocene dichloride; lithium di-tert-butylbiphenylide; dihydrogen peroxide; diisobutylaluminium hydride; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; lithium hexamethyldisilazane; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetone; toluene; 7.2: Wittig coupling;

DOI:10.1002/1521-3773(20021202)41:23<4560::AID-ANIE4560>3.0.CO;2-B

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → (2R,3R)-1-(tert-Butyl-dimethyl-silanyloxy)-4-{(2R,3R)-3-[(1R,2R)-1-(tert-butyl-dimethyl-silanyloxy)-2-methyl-4-triisopropylsilanyloxy-butyl]-oxiranyl}-3-(4-methoxy-benzyloxy)-butan-2-ol (500103-08-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 95 percent / NaH / tetrahydrofuran; dimethylformamide / 0 °C

2.1: O₃ / ethanol / -78 °C

2.2: dimethyl sulfide / ethanol

2.3: 95 percent / NaBH₄ / ethanol

3.1: 89 percent / I₂; imidazole; triphenylphosphine / CH₂Cl₂ / 0 °C

4.1: 89 percent / acetonitrile / 55 °C

5.1: lithium hexamethyldisilazide / tetrahydrofuran / -78 °C

5.2: 79 percent / tetrahydrofuran / -78 - 0 °C

6.1: 87 percent / K₂CO₃ / methanol; CH₂Cl₂

7.1: 95 percent / meta-chloroperoxybenzoic acid / CH₂Cl₂ / 0 °C

8.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / -78 °C

9.1: 79 percent / lithium di-tert-butylbiphenylide / tetrahydrofuran / -78 °C

With 1H-imidazole; 2,6-dimethylpyridine; lithium di-tert-butylbiphenylide; iodine; sodium hydride; potassium carbonate; ozone; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 5.2: Wittig coupling;

DOI:10.1002/1521-3773(20021202)41:23<4560::AID-ANIE4560>3.0.CO;2-B

upstream raw materials:

p-Methoxybenzyl bromide

(2R,3R)-2-Benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-hex-5-en-3-ol

(2R,3S)-2-Hydroxy-3-phenylsulfanylcarbonyl-butyric acid ethyl ester

(2R,3S)-3-Methyl-4-oxo-2-triphenylsilanyloxy-butyric acid ethyl ester

Downstream raw materials:

2-[(2S,3R,5S)-5-[(1R,2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-1-triethylsilanyloxy-5-triisopropylsilanyloxy-pentyl]-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-ylmethanesulfonyl]-benzothiazole

(1R,2R,3R)-1-[(2S,4R,5S)-5-(Benzothiazole-2-sulfonylmethyl)-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-2-(tert-butyl-dimethyl-silanyloxy)-3-methyl-5-triisopropylsilanyloxy-pentan-1-ol

(1R,2R,3R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(2S,4R,5R)-5-hydroxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yl]-3-methyl-5-triisopropylsilanyloxy-pentan-1-ol

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