Benzoic acid 2-benzenesulfonyl-2-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-1-phenyl-ethyl ester

Base Information

• Chemical Name: Benzoic acid 2-benzenesulfonyl-2-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-1-phenyl-ethyl ester
• CAS No.: 118888-91-8
• Molecular Formula: C₃₅H₄₄O₇SSi
• Molecular Weight: 636.882

Synonyms:

Chemical Property of Benzoic acid 2-benzenesulfonyl-2-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-1-phenyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Benzoic acid 2-benzenesulfonyl-2-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-1-phenyl-ethyl ester

There total 9 articles about Benzoic acid 2-benzenesulfonyl-2-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-1-phenyl-ethyl 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:

(+/-)-(3aα,4α,5β,6aα)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopentafuran-2-one (54423-47-1) → Benzoic acid 2-benzenesulfonyl-2-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-1-phenyl-ethyl ester (118888-91-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 63 percent / pyridine / 48 h / -18 °C

2: 1) t-BuOK / 1) DMSO, RT, 2) DMSO, 30 min

3: 75 percent / diisobutylaluminum hydride / toluene; CH₂Cl₂ / 0.5 h / -78 °C

4: 95 percent / BF₃*Et₂O / 2 h / -20 °C

5: 88 percent / imidazole / dimethylformamide / 0.17 h / 40 °C

6: 97 percent / 80percent m-chloroperbenzoic acid / CH₂Cl₂ / 1) -78 to 0 deg C, 30 min, 2) 0 deg C, 2 h

7: 1) n-butyllithium, 2) BF₃*Et₂O / 1) THF, hexane, -78 deg C, 10 min, 2) THF, hexane, -78 deg C, 5 min, 3) -18 deg C, 16 h; without BF₃*Et₂O

8: 1) n-butyllithium, 1,10-phenantroline / 1) THF, hexane, -78 deg C, 2) -78 to 20 deg C, 3) RT, 3 h

With pyridine; 1H-imidazole; n-butyllithium; 1,10-Phenanthroline; boron trifluoride diethyl etherate; potassium tert-butylate; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)86203-7

Reference yield:

thiophenol (108-98-5) → Benzoic acid 2-benzenesulfonyl-2-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-1-phenyl-ethyl ester (118888-91-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) t-BuOK / 1) DMSO, RT, 2) DMSO, 30 min

2: 75 percent / diisobutylaluminum hydride / toluene; CH₂Cl₂ / 0.5 h / -78 °C

3: 95 percent / BF₃*Et₂O / 2 h / -20 °C

4: 88 percent / imidazole / dimethylformamide / 0.17 h / 40 °C

5: 97 percent / 80percent m-chloroperbenzoic acid / CH₂Cl₂ / 1) -78 to 0 deg C, 30 min, 2) 0 deg C, 2 h

6: 1) n-butyllithium, 2) BF₃*Et₂O / 1) THF, hexane, -78 deg C, 10 min, 2) THF, hexane, -78 deg C, 5 min, 3) -18 deg C, 16 h; without BF₃*Et₂O

7: 1) n-butyllithium, 1,10-phenantroline / 1) THF, hexane, -78 deg C, 2) -78 to 20 deg C, 3) RT, 3 h

With 1H-imidazole; n-butyllithium; 1,10-Phenanthroline; boron trifluoride diethyl etherate; potassium tert-butylate; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(01)86203-7

Reference yield:

4β-(thiophenoxymethyl)-2ξ,5α-dihydroxy-3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopentafuran-2-one (86021-78-5,105455-57-0,105455-58-1,118919-53-2,118919-54-3) → Benzoic acid 2-benzenesulfonyl-2-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-1-phenyl-ethyl ester (118888-91-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / BF₃*Et₂O / 2 h / -20 °C

2: 88 percent / imidazole / dimethylformamide / 0.17 h / 40 °C

3: 97 percent / 80percent m-chloroperbenzoic acid / CH₂Cl₂ / 1) -78 to 0 deg C, 30 min, 2) 0 deg C, 2 h

4: 1) n-butyllithium, 2) BF₃*Et₂O / 1) THF, hexane, -78 deg C, 10 min, 2) THF, hexane, -78 deg C, 5 min, 3) -18 deg C, 16 h; without BF₃*Et₂O

5: 1) n-butyllithium, 1,10-phenantroline / 1) THF, hexane, -78 deg C, 2) -78 to 20 deg C, 3) RT, 3 h

With 1H-imidazole; n-butyllithium; 1,10-Phenanthroline; boron trifluoride diethyl etherate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)86203-7

upstream raw materials:

benzoyl chloride

5α-(t-butyldimethylsilyloxy)-2ξ-methoxy-4β--3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopentafuran

(+/-)-(3aα,4α,5β,6aα)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopentafuran-2-one

thiophenol

Downstream raw materials:

5α-(t-butyldimethylsilyloxy)-4β-(ethen-2'-phenyl)-2ξ-methoxy-3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopentafuran

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