(4S)-3-<(2S,3R,4S,5R,6S)-12-<<(benzyloxy)methyl>oxy>-5-(tert-butyldimethylsiloxy)-7,9-dioxo-3-methoxy-2,4,6,12-tetramethyltridecanoyl>-4-isopropyloxazolidin-2-one

Base Information

Chemical Name:(4S)-3-<(2S,3R,4S,5R,6S)-12-<<(benzyloxy)methyl>oxy>-5-(tert-butyldimethylsiloxy)-7,9-dioxo-3-methoxy-2,4,6,12-tetramethyltridecanoyl>-4-isopropyloxazolidin-2-one
CAS No.:112482-08-3
Molecular Formula:C₃₈H₆₃NO₉Si
Molecular Weight:706.005
Hs Code.:

(4S)-3-<(2S,3R,4S,5R,6S)-12-<<(benzyloxy)methyl>oxy>-5-(tert-butyldimethylsiloxy)-7,9-dioxo-3-methoxy-2,4,6,12-tetramethyltridecanoyl>-4-isopropyloxazolidin-2-one

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Chemical Property of (4S)-3-<(2S,3R,4S,5R,6S)-12-<<(benzyloxy)methyl>oxy>-5-(tert-butyldimethylsiloxy)-7,9-dioxo-3-methoxy-2,4,6,12-tetramethyltridecanoyl>-4-isopropyloxazolidin-2-one

Chemical Property:

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Technology Process of (4S)-3-<(2S,3R,4S,5R,6S)-12-<<(benzyloxy)methyl>oxy>-5-(tert-butyldimethylsiloxy)-7,9-dioxo-3-methoxy-2,4,6,12-tetramethyltridecanoyl>-4-isopropyloxazolidin-2-one

There total 14 articles about (4S)-3-<(2S,3R,4S,5R,6S)-12-<<(benzyloxy)methyl>oxy>-5-(tert-butyldimethylsiloxy)-7,9-dioxo-3-methoxy-2,4,6,12-tetramethyltridecanoyl>-4-isopropyloxazolidin-2-one 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:

: 624-97-5
2-methylpent-4-en-2-ol

: 112482-08-3
(4S)-3-<(2S,3R,4S,5R,6S)-12-<<(benzyloxy)methyl>oxy>-5-(tert-butyldimethylsiloxy)-7,9-dioxo-3-methoxy-2,4,6,12-tetramethyltridecanoyl>-4-isopropyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / N,N-diisopropylethylamine / 8 h / 0 °C

2: 77 percent / BH₃*SMe₂ / tetrahydrofuran / 2 h / Ambient temperature

3: 1.) oxalyl chloride/DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) 5 min

4: 1.) LDA / 1.) THF, -70 deg C, 45 min, 2.) from -70 to -40 deg C, 60 min

5: 1.) oxalyl chloride/DMSO, 2.) N,N-diisopropylethylamine / 1.) CH₂Cl₂, -70 deg C, 15 min, 2.) 5 min

With oxalyl dichloride; dimethylsulfide borane complex; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran;
DOI:10.1021/jo00240a022

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 112482-08-3
(4S)-3-<(2S,3R,4S,5R,6S)-12-<<(benzyloxy)methyl>oxy>-5-(tert-butyldimethylsiloxy)-7,9-dioxo-3-methoxy-2,4,6,12-tetramethyltridecanoyl>-4-isopropyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / N,N-diisopropylethylamine / 8 h / 0 °C

2: 77 percent / BH₃*SMe₂ / tetrahydrofuran / 2 h / Ambient temperature

3: 1.) oxalyl chloride/DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 15 min, 2.) 5 min

4: 1.) LDA / 1.) THF, -70 deg C, 45 min, 2.) from -70 to -40 deg C, 60 min

5: 1.) oxalyl chloride/DMSO, 2.) N,N-diisopropylethylamine / 1.) CH₂Cl₂, -70 deg C, 15 min, 2.) 5 min

With oxalyl dichloride; dimethylsulfide borane complex; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran;
DOI:10.1021/jo00240a022

Reference yield:

: 112482-00-5
methyl (2R,3S,4R)-3-hydroxy-2,4,5-trimethylhex-5-enoate

: 112482-08-3
(4S)-3-<(2S,3R,4S,5R,6S)-12-<<(benzyloxy)methyl>oxy>-5-(tert-butyldimethylsiloxy)-7,9-dioxo-3-methoxy-2,4,6,12-tetramethyltridecanoyl>-4-isopropyloxazolidin-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 72 percent / lutidine / CH₂Cl₂ / 3 h

2: 79 percent / DIBAH / diethyl ether / 2 h / 0 °C

3: 1.) oxalyl chloride/DMSO, 2.) N,N-diisopropylethylamine / 1.) CH₂Cl₂, -70 deg C, 20 min, 2.) 40 min

4: 1.) N,N-diisopropylethylamine, dibutylboron triflate / 1.) CH₂Cl₂, 1 h, 2.) a) -78 deg C, 30 min, b) RT, 2 h

5: 82 percent / di-tert-butylpyridine / CHCl₃ / 15 h / Heating

6: 1.) O₂, O₃, NaHCO₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) from 0 deg C to RT, 10 h

7: 1.) LDA / 1.) THF, -70 deg C, 45 min, 2.) from -70 to -40 deg C, 60 min

8: 1.) oxalyl chloride/DMSO, 2.) N,N-diisopropylethylamine / 1.) CH₂Cl₂, -70 deg C, 15 min, 2.) 5 min

With oxalyl dichloride; dimethylsulfide; lutidine; di-n-butylboryl trifluoromethanesulfonate; oxygen; diisobutylaluminium hydride; sodium hydrogencarbonate; ozone; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; Di-tert-butylpyridine; lithium diisopropyl amide; In diethyl ether; dichloromethane; chloroform;
DOI:10.1021/jo00240a022