[(2R,3S,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid ethyl ester

Base Information

Chemical Name:[(2R,3S,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid ethyl ester
CAS No.:273926-11-7
Molecular Formula:C₃₃H₄₈O₈Si
Molecular Weight:600.825
Hs Code.:

Synonyms:[(2R,3S,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid ethyl ester

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Chemical Property of [(2R,3S,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid ethyl ester

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Technology Process of [(2R,3S,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid ethyl ester

There total 7 articles about [(2R,3S,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid 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: 89.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 273926-10-6
((2R,3S,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-3-hydroxy-6-methoxy-octahydro-pyrano[3,2-b]pyran-2-yl)-acetic acid ethyl ester

: 273926-11-7
[(2R,3S,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid ethyl ester

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃;
DOI:10.1021/ol0000408

Reference yield:

: 90633-95-7,94827-31-3,90633-90-2
methyl 2,3-bis-O-benzyl-4-O-[(4-methoxyphenyl)methyl]-α-D-glucopyranoside

: 273926-11-7
[(2R,3S,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: 92 percent / I₂; PPh₃; imidazole / toluene

2.1: 74 percent / dimethylsulfoxide

3.1: 77 percent / DDQ / H₂O; CH₂Cl₂

4.1: 99 percent / N-methylmorpholine / CH₂Cl₂

5.1: Bu₃SnH; AIBN / toluene / 10 h / 80 °C

5.2: 85 percent / p-TsOH / CH₂Cl₂ / 1.5 h

6.1: O₃ / -70 °C

6.2: 92 percent / NaBH₄ / methanol; CH₂Cl₂ / -70 - 20 °C

7.1: 89 percent / i-Pr₂EtN / CH₂Cl₂ / 0 °C

With 4-methyl-morpholine; 1H-imidazole; 2,2'-azobis(isobutyronitrile); iodine; tri-n-butyl-tin hydride; ozone; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; dimethyl sulfoxide; toluene; 1.1: Substitution / 2.1: Substitution / 3.1: Substitution / 4.1: Hetero-Michael addition / 5.1: Cycloaddition / 5.2: Substitution / 6.1: Ozonolyis / 6.2: Reduction / 7.1: Substitution;
DOI:10.1021/ol0000408

Reference yield:

: 273926-19-5
(2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-2-prop-2-ynyl-tetrahydro-pyran-3-ol

: 273926-11-7
[(2R,3S,4aR,6S,7R,8S,8aR)-7,8-Bis-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-6-methoxy-octahydro-pyrano[3,2-b]pyran-2-yl]-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 99 percent / N-methylmorpholine / CH₂Cl₂

2.1: Bu₃SnH; AIBN / toluene / 10 h / 80 °C

2.2: 85 percent / p-TsOH / CH₂Cl₂ / 1.5 h

3.1: O₃ / -70 °C

3.2: 92 percent / NaBH₄ / methanol; CH₂Cl₂ / -70 - 20 °C

4.1: 89 percent / i-Pr₂EtN / CH₂Cl₂ / 0 °C

With 4-methyl-morpholine; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; ozone; N-ethyl-N,N-diisopropylamine; In dichloromethane; toluene; 1.1: Hetero-Michael addition / 2.1: Cycloaddition / 2.2: Substitution / 3.1: Ozonolyis / 3.2: Reduction / 4.1: Substitution;
DOI:10.1021/ol0000408