Acetic acid (2S,4R,5R,6S,8S,10R,11S)-2-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-5,8,11-trimethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester

Base Information

Chemical Name:Acetic acid (2S,4R,5R,6S,8S,10R,11S)-2-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-5,8,11-trimethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester
CAS No.:873850-97-6
Molecular Formula:C₂₉H₄₈O₆Si
Molecular Weight:520.782
Hs Code.:

Acetic acid (2S,4R,5R,6S,8S,10R,11S)-2-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-5,8,11-trimethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester

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Chemical Property of Acetic acid (2S,4R,5R,6S,8S,10R,11S)-2-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-5,8,11-trimethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester

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Technology Process of Acetic acid (2S,4R,5R,6S,8S,10R,11S)-2-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-5,8,11-trimethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester

There total 8 articles about Acetic acid (2S,4R,5R,6S,8S,10R,11S)-2-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-5,8,11-trimethyl-1,7-dioxa-spiro[5.5]undec-4-yl 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: 4.2%

: C₂₅H₄₃BO

: 56816-01-4
ethyl (S)-3-hydroxybutyrate

: 108-24-7
acetic anhydride

: 18162-48-6
tert-butyldimethylsilyl chloride

: 215160-79-5
(3S)-5-benzyloxy-3-(4-methoxybenzyloxy)pentanal

: 873850-97-6
Acetic acid (2S,4R,5R,6S,8S,10R,11S)-2-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-5,8,11-trimethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester

Guidance literature:: Multistep reaction;
DOI:10.1002/ejoc.200500605

Reference yield:

: (4S)-4-(4-methoxybenzyloxy)-6-(benzyloxy)hexane-1,2-diol

: 873850-97-6
Acetic acid (2S,4R,5R,6S,8S,10R,11S)-2-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-5,8,11-trimethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 96 percent / NaIO₄ / CH₂Cl₂; H₂O / 6 h / 20 °C

With sodium periodate; In dichloromethane; water;
DOI:10.1002/ejoc.200500605

Reference yield:

: 4799-68-2
3-benzyloxypropan-1-ol

: 873850-97-6
Acetic acid (2S,4R,5R,6S,8S,10R,11S)-2-(2-benzyloxy-ethyl)-10-(tert-butyl-dimethyl-silanyloxy)-5,8,11-trimethyl-1,7-dioxa-spiro[5.5]undec-4-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 92 percent / oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: (+)-Ipc₂BCl / tetrahydrofuran / -78 - 20 °C

2.2: tetrahydrofuran / -78 - 20 °C

2.3: 86 percent / NaOH; H₂O₂ / tetrahydrofuran; H₂O / 0.17 h / 0 °C

3.1: hexane; CH₂Cl₂ / 0.5 h

3.2: 71 percent / BF₃*OEt₂ / hexane; CH₂Cl₂ / 1 h / 0 °C

4.1: 85 percent / 4-N-methylmorpholine N-oxide; OsO₄ / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

5.1: 96 percent / NaIO₄ / CH₂Cl₂; H₂O / 6 h / 20 °C

With sodium periodate; osmium(VIII) oxide; (+)-β-chlorodiisopinocampheylborane; oxalyl dichloride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; water; tert-butyl alcohol;
DOI:10.1002/ejoc.200500605