[1S,5S,6S,9S,9(1R)]-9-benzyloxy-9-[2-(tert-butyldiphenylsilyl)oxy-1-methyl]ethyl-5-iodo-1-methyl-7-oxabicyclo[4.3.0]nonan-8-one

Base Information

Chemical Name:[1S,5S,6S,9S,9(1R)]-9-benzyloxy-9-[2-(tert-butyldiphenylsilyl)oxy-1-methyl]ethyl-5-iodo-1-methyl-7-oxabicyclo[4.3.0]nonan-8-one
CAS No.:1519887-32-1
Molecular Formula:C₃₅H₄₃IO₄Si
Molecular Weight:682.714
Hs Code.:

Synonyms:[1S,5S,6S,9S,9(1R)]-9-benzyloxy-9-[2-(tert-butyldiphenylsilyl)oxy-1-methyl]ethyl-5-iodo-1-methyl-7-oxabicyclo[4.3.0]nonan-8-one

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Chemical Property of [1S,5S,6S,9S,9(1R)]-9-benzyloxy-9-[2-(tert-butyldiphenylsilyl)oxy-1-methyl]ethyl-5-iodo-1-methyl-7-oxabicyclo[4.3.0]nonan-8-one

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Technology Process of [1S,5S,6S,9S,9(1R)]-9-benzyloxy-9-[2-(tert-butyldiphenylsilyl)oxy-1-methyl]ethyl-5-iodo-1-methyl-7-oxabicyclo[4.3.0]nonan-8-one

There total 8 articles about [1S,5S,6S,9S,9(1R)]-9-benzyloxy-9-[2-(tert-butyldiphenylsilyl)oxy-1-methyl]ethyl-5-iodo-1-methyl-7-oxabicyclo[4.3.0]nonan-8-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: 77.0%

: 1519887-23-0
[2S,2(1S),3R]-2-benzyloxy-4-(tert-butyldiphenylsilyl)oxy-3-methyl-2-(1-methylcyclohex-2-en-1-yl)butanoic acid

: 1519887-32-1
[1S,5S,6S,9S,9(1R)]-9-benzyloxy-9-[2-(tert-butyldiphenylsilyl)oxy-1-methyl]ethyl-5-iodo-1-methyl-7-oxabicyclo[4.3.0]nonan-8-one

Guidance literature:: With iodine; sodium hydrogencarbonate; In water; acetonitrile; at 0 ℃; for 1h;
DOI:10.1021/jo402537u

Reference yield:

: 1519887-08-1
(2R,3R)-2-benzyloxy-4-(tert-butyldiphenylsilyl)oxy-3-methyl-1-butanal

: 1519887-32-1
[1S,5S,6S,9S,9(1R)]-9-benzyloxy-9-[2-(tert-butyldiphenylsilyl)oxy-1-methyl]ethyl-5-iodo-1-methyl-7-oxabicyclo[4.3.0]nonan-8-one

Guidance literature:: Multi-step reaction with 4 steps

1: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / tert-butyl alcohol; water / 3 h

2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 0 - 20 °C

3: chloro-trimethyl-silane; lithium diisopropyl amide / tetrahydrofuran / 12 h / -78 - 20 °C

4: iodine; sodium hydrogencarbonate / water; acetonitrile / 1 h / 0 °C

With dmap; sodium chlorite; sodium dihydrogenphosphate; chloro-trimethyl-silane; 2-methyl-but-2-ene; iodine; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo402537u

Reference yield:

: 131484-40-7
((2S,3S)-3-(((tert-butyldiphenylsilyl)oxy)methyl)oxiran-2-yl)methanol

: 1519887-32-1
[1S,5S,6S,9S,9(1R)]-9-benzyloxy-9-[2-(tert-butyldiphenylsilyl)oxy-1-methyl]ethyl-5-iodo-1-methyl-7-oxabicyclo[4.3.0]nonan-8-one

Guidance literature:: Multi-step reaction with 8 steps

1: n-heptane; pentane / 3 h / 0 °C

2: pyridinium p-toluenesulfonate / dichloromethane / 48 h

3: diisobutylaluminium hydride / dichloromethane; hexane / 9 h / -78 °C

4: Dess-Martin periodane / dichloromethane / 1 h / 0 °C

5: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / tert-butyl alcohol; water / 3 h

6: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 18 h / 0 - 20 °C

7: chloro-trimethyl-silane; lithium diisopropyl amide / tetrahydrofuran / 12 h / -78 - 20 °C

8: iodine; sodium hydrogencarbonate / water; acetonitrile / 1 h / 0 °C

With dmap; sodium chlorite; sodium dihydrogenphosphate; chloro-trimethyl-silane; 2-methyl-but-2-ene; iodine; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; hexane; n-heptane; dichloromethane; water; acetonitrile; tert-butyl alcohol; pentane;
DOI:10.1021/jo402537u