(2R,3R,4S)-3,4-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-5,5-bis-ethylsulfanyl-pentan-2-ol

Base Information

Chemical Name:(2R,3R,4S)-3,4-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-5,5-bis-ethylsulfanyl-pentan-2-ol
CAS No.:651321-33-4
Molecular Formula:C₂₉H₄₆O₄S₂Si
Molecular Weight:550.899
Hs Code.:

Synonyms:(2R,3R,4S)-3,4-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-5,5-bis-ethylsulfanyl-pentan-2-ol

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Chemical Property of (2R,3R,4S)-3,4-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-5,5-bis-ethylsulfanyl-pentan-2-ol

Chemical Property:

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Technology Process of (2R,3R,4S)-3,4-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-5,5-bis-ethylsulfanyl-pentan-2-ol

There total 1 articles about (2R,3R,4S)-3,4-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-5,5-bis-ethylsulfanyl-pentan-2-ol 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: 87.0%

: 138535-75-8
2,3-di-O-benzyl-D-arabinose diethyl dithioacetal

: 18162-48-6
tert-butyldimethylsilyl chloride

: 651321-33-4
(2R,3R,4S)-3,4-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-5,5-bis-ethylsulfanyl-pentan-2-ol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 12h;
DOI:10.1081/CAR-120026470

Reference yield:

: 651321-33-4
(2R,3R,4S)-3,4-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-5,5-bis-ethylsulfanyl-pentan-2-ol

: 651321-34-5
2,3-di-O-benzyl-5-O-tert-butyl(dimethyl)silyl-D-arabinose

Guidance literature:: With mercury dichloride; mercury(II) oxide; In water; acetone; at 60 ℃; for 3h;
DOI:10.1081/CAR-120026470

Reference yield:

: 651321-33-4
(2R,3R,4S)-3,4-Bis-benzyloxy-1-(tert-butyl-dimethyl-silanyloxy)-5,5-bis-ethylsulfanyl-pentan-2-ol

: 651321-48-1
(2R,3R,4R,5R)-N-[(1,1-dimethylethoxy)carbonyl]-2-[(phenylmethoxy)methyl]-3,4-bis(phenylmethyloxy)-5-(1-oxodecan-11-yl)pyrrolidine

Guidance literature:: Multi-step reaction with 15 steps

1: HgO; HgCl₂ / acetone; H₂O / 3 h / 60 °C

2: tetrahydrofuran / 3 h / 20 °C

3: 86 percent / HCl / methanol / 3 h / 0 °C

4: 70 percent / p-TsOH / CH₂Cl₂ / 1 h / -20 - 10 °C

5: CH₂Cl₂ / 1.58 h / 0 - 20 °C

6: 80 percent / NaN₃ / dimethylformamide / 18 h / 60 °C

7: 89 percent / AlCl₃; BH₃*NMe₃ / tetrahydrofuran / 3 h / 0 °C

8: 88 percent / PPh₃; DEAD / tetrahydrofuran / 18 h / 20 °C

9: 85 percent / PPh₃; H₂O / tetrahydrofuran / 4 h / 60 °C

10: 76 percent / NaOH / methanol / 0 - 20 °C

11: 80 percent / Et₃N / tetrahydrofuran / 0.03 h / 0 - 20 °C

12: Et₃N / CH₂Cl₂ / 1.58 h / 0 - 20 °C

13: t-BuOK / tetrahydrofuran; CH₂Cl₂ / 18 h / 20 °C

14: K₂OsO₄*2H₂O; NMO / acetone; H₂O / 3 h / 20 °C

15: NaIO₄ / diethyl ether; H₂O / 2 h / 20 °C

With hydrogenchloride; sodium hydroxide; potassium osmate(VI); sodium periodate; aluminium trichloride; sodium azide; N-methyl-2-indolinone; trimethylamine-borane; potassium tert-butylate; water; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; mercury dichloride; mercury(II) oxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; 2: Grignard addition / 8: Mitsunobu reaction / 9: Staudinger reduction;
DOI:10.1081/CAR-120026470