(R)-((1R,2S,5R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopentyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol

Base Information

• Chemical Name: (R)-((1R,2S,5R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopentyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol
• CAS No.: 126019-49-6
• Molecular Formula: C₃₀H₅₂O₅Si
• Molecular Weight: 520.825
• Mol file: 126019-49-6.mol

Synonyms:

Chemical Property of (R)-((1R,2S,5R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopentyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-((1R,2S,5R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopentyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol

There total 36 articles about (R)-((1R,2S,5R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopentyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol 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:

methyl 1-methyl-2-oxocyclopentane-1-carboxylate (30680-84-3) → (S)-((1R,2S,5R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopentyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol (126019-49-6,126107-25-3,126107-49-1,126107-99-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 1) sodium hydride / 1) THF, r.t., 1 h, 2) THF, 15 h

2: 100 percent / trifluoroacetic acid / CH₂Cl₂ / 24 h / Ambient temperature

3: 57 percent / BH₃*THF / tetrahydrofuran / 20 h / Ambient temperature

4: 87 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

5: 96 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

6: 93 percent / H₂ / 3(py)>PF₆ / CH₂Cl₂ / 3 h / Ambient temperature

7: 91 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.08 h / -78 °C

8: 1) t-BuLi / 1) ether, -78 deg C, 1.5 h, 2) 5 h

9: 66 percent / NH₃, lithium / diethyl ether / 1.5 h / Heating

10: 75 percent / silver carbonate on Celite, / benzene / 14 h / Heating

11: 90 percent / potassium carbonate, H₂ / 5percent Rh/C / ethyl acetate / 14 h

12: 90 percent / LAH / diethyl ether / 1 h

13: 1) NaH / 1) THF, r.t., 1.5 h, 2) 15 h

With 1H-imidazole; lithium aluminium tetrahydride; borane-THF; oxalyl dichloride; ammonia; hydrogen; tert.-butyl lithium; lithium; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; silver carbonate; trifluoroacetic acid; (η4-1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate; Rh on carbon; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jo00297a024

Reference yield:

methyl 1-methyl-2-oxocyclopentane-1-carboxylate (30680-84-3) → (R)-((1R,2S,5R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopentyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol (126019-49-6,126107-25-3,126107-49-1,126107-99-1)

Guidance literature:

Multi-step reaction with 13 steps

1: 1) sodium hydride / 1) THF, r.t., 1 h, 2) THF, 15 h

2: 100 percent / trifluoroacetic acid / CH₂Cl₂ / 24 h / Ambient temperature

3: 57 percent / BH₃*THF / tetrahydrofuran / 20 h / Ambient temperature

4: 87 percent / imidazole / dimethylformamide / 1.5 h / Ambient temperature

5: 96 percent / LiAlH₄ / diethyl ether / 1 h / 0 °C

6: 93 percent / H₂ / 3(py)>PF₆ / CH₂Cl₂ / 3 h / Ambient temperature

7: 91 percent / oxalyl chloride, DMSO, Et₃N / CH₂Cl₂ / 0.08 h / -78 °C

8: 1) t-BuLi / 1) ether, -78 deg C, 1.5 h, 2) 5 h

9: NH₃, lithium / diethyl ether / 1.5 h / Heating

10: 88 percent / silver carbonate on Celite, / CHCl₃ / 8 h / Heating

11: 90 percent / potassium carbonate, H₂ / 5percent Rh/C / ethyl acetate / 14 h

12: 92 percent / LAH / diethyl ether / 1 h

13: 1) NaH / 1) THF, r.t., 1 h, 2) 2 h

With 1H-imidazole; lithium aluminium tetrahydride; borane-THF; oxalyl dichloride; ammonia; hydrogen; tert.-butyl lithium; lithium; sodium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; silver carbonate; trifluoroacetic acid; (η4-1,5-cyclooctadiene)(pyridine)(tricyclohexylphosphine)iridium(I) hexafluorophosphate; Rh on carbon; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00297a024

Reference yield:

3-ethoxycyclopent-2-en-1-one (22627-70-9) → (R)-((1R,2S,5R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopentyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methanol (126019-49-6,126107-25-3,126107-49-1,126107-99-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 1) n-BuLi / 1) THF, hexane, -78 deg C, 15 min, 2) THF, -78 deg C, 45 min

2: 86 percent / pyridine, pyridinium bromide perbromide / CH₂Cl₂ / 14 h / 3 °C

3: 19.00 g / cerium(III) chloride heptahydrate, sodium borohydride / methanol / 0.33 h

4: diisopropylethylamine / CH₂Cl₂ / 20 h / Ambient temperature

5: 1) t-BuLi / 1) ether, -78 deg C, 1.5 h, 2) 5 h

6: NH₃, lithium / diethyl ether / 1.5 h / Heating

7: 88 percent / silver carbonate on Celite, / CHCl₃ / 8 h / Heating

8: 90 percent / potassium carbonate, H₂ / 5percent Rh/C / ethyl acetate / 14 h

9: 92 percent / LAH / diethyl ether / 1 h

10: 1) NaH / 1) THF, r.t., 1 h, 2) 2 h

With pyridine; sodium tetrahydroborate; lithium aluminium tetrahydride; n-butyllithium; cerium(III) chloride; ammonia; hydrogen; tert.-butyl lithium; pyridinium hydrobromide perbromide; lithium; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; silver carbonate; Rh on carbon; In methanol; diethyl ether; dichloromethane; chloroform; ethyl acetate;

DOI:10.1021/jo00297a024

upstream raw materials:

(S)-{(1R,2S)-2-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-((1R,2S,5R)-2-hydroxymethyl-5-methoxymethoxy-cyclopentyl)-methanol

benzyl bromide

3-ethoxycyclopent-2-en-1-one

methyl 1-methyl-2-oxocyclopentane-1-carboxylate

Downstream raw materials:

Dithiocarbonic acid O-((S)-((1S,2S,5R)-2-benzyloxymethyl-5-methoxymethoxy-cyclopentyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methyl) ester S-methyl ester

Dithiocarbonic acid O-((R)-((1S,2S,5R)-2-benzyloxymethyl-5-methoxymethoxy-cyclopentyl)-{(1R,2S)-2-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1-methyl-cyclopentyl}-methyl) ester S-methyl ester

{2-[(1R,2R)-2-((1R,2R)-2-Benzyloxymethyl-5-methoxymethoxy-cyclopentylmethyl)-2-methyl-cyclopentyl]-ethoxy}-tert-butyl-dimethyl-silane