(2R,3R,4R,4aS,9aS)-4-((4-bromobenzyl)oxy)-2-(2-(methylsulfinyl)-2-(methylthio)ethyl)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepine

Base Information

Chemical Name:(2R,3R,4R,4aS,9aS)-4-((4-bromobenzyl)oxy)-2-(2-(methylsulfinyl)-2-(methylthio)ethyl)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepine
CAS No.:784157-58-0
Molecular Formula:C₃₁H₃₅BrO₅S₂
Molecular Weight:631.652
Hs Code.:

(2R,3R,4R,4aS,9aS)-4-((4-bromobenzyl)oxy)-2-(2-(methylsulfinyl)-2-(methylthio)ethyl)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepine

Synonyms:(2R,3R,4R,4aS,9aS)-4-((4-bromobenzyl)oxy)-2-(2-(methylsulfinyl)-2-(methylthio)ethyl)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepine

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Chemical Property of (2R,3R,4R,4aS,9aS)-4-((4-bromobenzyl)oxy)-2-(2-(methylsulfinyl)-2-(methylthio)ethyl)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepine

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Technology Process of (2R,3R,4R,4aS,9aS)-4-((4-bromobenzyl)oxy)-2-(2-(methylsulfinyl)-2-(methylthio)ethyl)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepine

There total 16 articles about (2R,3R,4R,4aS,9aS)-4-((4-bromobenzyl)oxy)-2-(2-(methylsulfinyl)-2-(methylthio)ethyl)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepine 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:

: 33577-16-1
methyl methylsulfinylmethyl sulfide

: 784157-69-3
Trifluoro-methanesulfonic acid (2R,3R,4R,4aS,9aS)-4-(4-bromo-benzyloxy)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-1,5-dioxa-benzocyclohepten-2-ylmethyl ester

: 784157-58-0
(2R,3R,4R,4aS,9aS)-4-((4-bromobenzyl)oxy)-2-(2-(methylsulfinyl)-2-(methylthio)ethyl)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepine

Guidance literature:: With n-butyllithium; In tetrahydrofuran; at -20 - 0 ℃;
DOI:10.1016/j.tetlet.2004.07.145

Reference yield:

: 259882-15-0
allyl 4,6-O-benzylidene-D-glucopyranoside

: 784157-58-0
(2R,3R,4R,4aS,9aS)-4-((4-bromobenzyl)oxy)-2-(2-(methylsulfinyl)-2-(methylthio)ethyl)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepine

Guidance literature:: Multi-step reaction with 16 steps

1.1: 95 percent / imidazole / dimethylformamide / 23 °C

2.1: 99 percent / Et₃Al / [NiCl₂(dpp)] / toluene / 0 - 24 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

4.1: diethyl ether / -78 °C

5.1: 80 percent / BF₃*OEt₂ / CH₂Cl₂ / -20 °C

6.1: mCPBA / CH₂Cl₂ / 0 °C

6.2: 80 percent / Et₃SiH; BF₃*OEt₂ / 0 °C

7.1: 92 percent / PPTS / benzene / Heating

8.1: 90 percent / TBAF / tetrahydrofuran / 23 °C

9.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

10.1: NaH; Bu₄NI / tetrahydrofuran / 0 °C

11.1: (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / Heating

12.1: TBAF / tetrahydrofuran / 23 °C

13.1: NaH; Bu₄NI / tetrahydrofuran / 24 °C

14.1: LiAlH₄; AlCl₃ / CH₂Cl₂; diethyl ether / 24 °C

15.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

16.1: BuLi / tetrahydrofuran / -20 - 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; triethylaluminum; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; Grubbs catalyst first generation; [NiCl₂(dpp)]; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 3.1: Swern oxidation / 4.1: Grignard reaction;
DOI:10.1016/j.tetlet.2004.07.145

Reference yield:

: 4,6-O-benzylidene-2,3-O-(3,5-diisopropyl-2,6-dimethyl-4-oxa-3,5-disilaheptane-3,5-diyl)-D-glucopyranose

: 784157-58-0
(2R,3R,4R,4aS,9aS)-4-((4-bromobenzyl)oxy)-2-(2-(methylsulfinyl)-2-(methylthio)ethyl)-3-(naphthalen-2-ylmethoxy)-3,4,4a,6,9,9a-hexahydro-2H-pyrano[3,2-b]oxepine

Guidance literature:: Multi-step reaction with 14 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: diethyl ether / -78 °C

3.1: 80 percent / BF₃*OEt₂ / CH₂Cl₂ / -20 °C

4.1: mCPBA / CH₂Cl₂ / 0 °C

4.2: 80 percent / Et₃SiH; BF₃*OEt₂ / 0 °C

5.1: 92 percent / PPTS / benzene / Heating

6.1: 90 percent / TBAF / tetrahydrofuran / 23 °C

7.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

8.1: NaH; Bu₄NI / tetrahydrofuran / 0 °C

9.1: (Cy₃P)2Cl₂Ru=CHPh / CH₂Cl₂ / Heating

10.1: TBAF / tetrahydrofuran / 23 °C

11.1: NaH; Bu₄NI / tetrahydrofuran / 24 °C

12.1: LiAlH₄; AlCl₃ / CH₂Cl₂; diethyl ether / 24 °C

13.1: 2,6-lutidine / CH₂Cl₂ / -78 °C

14.1: BuLi / tetrahydrofuran / -20 - 0 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; oxalyl dichloride; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; benzene; 1.1: Swern oxidation / 2.1: Grignard reaction;
DOI:10.1016/j.tetlet.2004.07.145