(2S,3S,4R,5R,6R)-3,4-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5-(4-bromo-benzyloxy)-6-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-tetrahydro-pyran

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Chemical Name:(2S,3S,4R,5R,6R)-3,4-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5-(4-bromo-benzyloxy)-6-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-tetrahydro-pyran
CAS No.:482646-95-7
Molecular Formula:C₃₉H₄₅BrO₆S₂
Molecular Weight:753.819
Hs Code.:

Synonyms:(2S,3S,4R,5R,6R)-3,4-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5-(4-bromo-benzyloxy)-6-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-tetrahydro-pyran

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Chemical Property of (2S,3S,4R,5R,6R)-3,4-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5-(4-bromo-benzyloxy)-6-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-tetrahydro-pyran

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Technology Process of (2S,3S,4R,5R,6R)-3,4-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5-(4-bromo-benzyloxy)-6-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-tetrahydro-pyran

There total 9 articles about (2S,3S,4R,5R,6R)-3,4-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5-(4-bromo-benzyloxy)-6-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-tetrahydro-pyran 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: 82.0%

: 33577-16-1
methyl methylsulfinylmethyl sulfide

: 482647-03-0
(2S,3S,4R,5S,6S)-3,4-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5-(4-bromo-benzyloxy)-6-iodomethyl-tetrahydro-pyran

: 482646-95-7
(2S,3S,4R,5R,6R)-3,4-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5-(4-bromo-benzyloxy)-6-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-tetrahydro-pyran

Guidance literature:: methyl methylsulfinylmethyl sulfide; With n-butyllithium; In tetrahydrofuran; at -20 ℃; for 0.75h;

(2S,3S,4R,5S,6S)-3,4-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5-(4-bromo-benzyloxy)-6-iodomethyl-tetrahydro-pyran; In tetrahydrofuran; at 22 ℃; for 0.75h;
DOI:10.1055/s-2002-34904

Reference yield:

: 873-75-6
4-bromobenzenemethanol

: 482646-95-7
(2S,3S,4R,5R,6R)-3,4-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5-(4-bromo-benzyloxy)-6-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH; TBAI / tetrahydrofuran / 3 h / 24 °C

2.1: TBAF / tetrahydrofuran / 6 h / 24 °C

3.1: 90 percent / I₂; PPh₃; imidazole / benzene / 0.5 h / 23 °C

4.1: BuLi / tetrahydrofuran / 0.75 h / -20 °C

4.2: 82 percent / tetrahydrofuran / 0.75 h / 22 °C

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; triphenylphosphine; In tetrahydrofuran; benzene;
DOI:10.1055/s-2002-34904

Reference yield:

: 100-39-0
benzyl bromide

: 482646-95-7
(2S,3S,4R,5R,6R)-3,4-Bis-benzyloxy-2-(2-benzyloxy-ethyl)-5-(4-bromo-benzyloxy)-6-(2-methanesulfinyl-2-methylsulfanyl-ethyl)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 7 steps

1.1: 99 percent / NaH; TBAI; t-BuOK / tetrahydrofuran / 20 h / 24 °C

2.1: 98 percent / aq. HCl / tetrahydrofuran / 17 h / 25 °C

3.1: 99 percent / DMAP; Et₃N / CH₂Cl₂ / 3.5 h / 24 °C

4.1: NaH; TBAI / tetrahydrofuran / 3 h / 24 °C

5.1: TBAF / tetrahydrofuran / 6 h / 24 °C

6.1: 90 percent / I₂; PPh₃; imidazole / benzene / 0.5 h / 23 °C

7.1: BuLi / tetrahydrofuran / 0.75 h / -20 °C

7.2: 82 percent / tetrahydrofuran / 0.75 h / 22 °C

With 1H-imidazole; hydrogenchloride; dmap; n-butyllithium; potassium tert-butylate; tetrabutyl ammonium fluoride; iodine; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1055/s-2002-34904