Methanesulfonic acid 1-{benzenesulfonyl-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-methyl}-2-(tert-butyl-dimethyl-silanyloxy)-heptyl ester

Base Information

• Chemical Name: Methanesulfonic acid 1-{benzenesulfonyl-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-methyl}-2-(tert-butyl-dimethyl-silanyloxy)-heptyl ester
• CAS No.: 118888-90-7
• Molecular Formula: C₃₅H₆₄O₉S₂Si₂
• Molecular Weight: 749.191

Synonyms:Methanesulfonic acid 1-{benzenesulfonyl-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-methyl}-2-(tert-butyl-dimethyl-silanyloxy)-heptyl ester

Chemical Property of Methanesulfonic acid 1-{benzenesulfonyl-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-methyl}-2-(tert-butyl-dimethyl-silanyloxy)-heptyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Methanesulfonic acid 1-{benzenesulfonyl-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-methyl}-2-(tert-butyl-dimethyl-silanyloxy)-heptyl ester

There total 9 articles about Methanesulfonic acid 1-{benzenesulfonyl-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-methyl}-2-(tert-butyl-dimethyl-silanyloxy)-heptyl 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: 80.0%

methanesulfonyl chloride (124-63-0) + 4β-<(1'ξ-benzenesulphonyl)-2'ξ-hydroxy-3'ξ-(t-butyldimethylsilyloxy)-1'-octyl>-5α-(t-butyldimethylsilyloxy)-2ξ-methoxy-3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopentafuran (105394-05-6) → Methanesulfonic acid 1-{benzenesulfonyl-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-methyl}-2-(tert-butyl-dimethyl-silanyloxy)-heptyl ester (118888-90-7)

Guidance literature:

With pyridine; at -10 - 0 ℃; for 16h;

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

Reference yield:

(+/-)-(3aα,4α,5β,6aα)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopentafuran-2-one (54423-47-1) → Methanesulfonic acid 1-{benzenesulfonyl-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-methyl}-2-(tert-butyl-dimethyl-silanyloxy)-heptyl ester (118888-90-7)

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 / multistep reaction; var. oxo compounds, var. solv, time and temp; further reag.: LDA

8: 80 percent / pyridine / 16 h / -10 - 0 °C

With pyridine; 1H-imidazole; n-butyllithium; 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) → Methanesulfonic acid 1-{benzenesulfonyl-[(3aS,4S,5S,6aR)-5-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-hexahydro-cyclopenta[b]furan-4-yl]-methyl}-2-(tert-butyl-dimethyl-silanyloxy)-heptyl ester (118888-90-7)

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 / multistep reaction; var. oxo compounds, var. solv, time and temp; further reag.: LDA

7: 80 percent / pyridine / 16 h / -10 - 0 °C

With pyridine; 1H-imidazole; n-butyllithium; 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

upstream raw materials:

methanesulfonyl chloride

4β-<(1'ξ-benzenesulphonyl)-2'ξ-hydroxy-3'ξ-(t-butyldimethylsilyloxy)-1'-octyl>-5α-(t-butyldimethylsilyloxy)-2ξ-methoxy-3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopentafuran

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

thiophenol

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