(4S,6S)-4-{(4R,6S)-6-[(2S,4S,6R)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-6-iodomethyl-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Base Information

Chemical Name:(4S,6S)-4-{(4R,6S)-6-[(2S,4S,6R)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-6-iodomethyl-2,2-dimethyl-[1,3]dioxane-4-carbonitrile
CAS No.:189195-79-7
Molecular Formula:C₃₆H₅₈INO₇Si
Molecular Weight:771.849
Hs Code.:

(4S,6S)-4-{(4R,6S)-6-[(2S,4S,6R)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-6-iodomethyl-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

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Chemical Property of (4S,6S)-4-{(4R,6S)-6-[(2S,4S,6R)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-6-iodomethyl-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

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Technology Process of (4S,6S)-4-{(4R,6S)-6-[(2S,4S,6R)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-6-iodomethyl-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

There total 7 articles about (4S,6S)-4-{(4R,6S)-6-[(2S,4S,6R)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-6-iodomethyl-2,2-dimethyl-[1,3]dioxane-4-carbonitrile 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:

: 34591-97-4
3-(benzyloxy)propanal dimethyl acetal

: 189195-79-7
(4S,6S)-4-{(4R,6S)-6-[(2S,4S,6R)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-6-iodomethyl-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Guidance literature:: Multi-step reaction with 6 steps

1: camphorsulfonic acid / CH₂Cl₂

2: 1.) BF₃*OEt₂, acetic acid, 2.) 4-dimethylaminopyridine, triethylamine / 1.) cyclohexane, 23 deg C

3: 1.) (DHQD)2-PYR, OsO₄, K₃Fe(CN)6

5: 1.) LiNEt₂, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, -78 deg C, 2.) -78 -> 20 deg C

6: 1.) tetrabutylammonium fluoride, 2.) I₂, triphenylphosphine, imidazole / 1.) 0 deg C, 2.) diethyl ether, benzene

With 1H-imidazole; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; osmium(VIII) oxide; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; lithium diethylamide; tetrabutyl ammonium fluoride; iodine; acetic acid; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); In dichloromethane;
DOI:10.1021/jo970380f

Reference yield:

: 189195-78-6
(4S,6S)-4-{(4R,6S)-6-[(2S,4S,6R)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-2,2-dimethyl-6-triisopropylsilanyloxymethyl-[1,3]dioxane-4-carbonitrile

: 189195-79-7
(4S,6S)-4-{(4R,6S)-6-[(2S,4S,6R)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-6-iodomethyl-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Guidance literature:: With 1H-imidazole; tetrabutyl ammonium fluoride; iodine; triphenylphosphine; Yield given. Multistep reaction; 1.) 0 deg C, 2.) diethyl ether, benzene;
DOI:10.1021/jo970380f

Reference yield:

: 189195-74-2
(4R,6R)-4,6-Diallyl-2-(2-benzyloxy-ethyl)-[1,3]dioxane

: 189195-79-7
(4S,6S)-4-{(4R,6S)-6-[(2S,4S,6R)-6-(2-Benzyloxy-ethyl)-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-ylmethyl]-2,2-dimethyl-[1,3]dioxan-4-ylmethyl}-6-iodomethyl-2,2-dimethyl-[1,3]dioxane-4-carbonitrile

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) BF₃*OEt₂, acetic acid, 2.) 4-dimethylaminopyridine, triethylamine / 1.) cyclohexane, 23 deg C

2: 1.) (DHQD)2-PYR, OsO₄, K₃Fe(CN)6

4: 1.) LiNEt₂, 2.) 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1.) THF, -78 deg C, 2.) -78 -> 20 deg C

5: 1.) tetrabutylammonium fluoride, 2.) I₂, triphenylphosphine, imidazole / 1.) 0 deg C, 2.) diethyl ether, benzene

With 1H-imidazole; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; osmium(VIII) oxide; hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether; boron trifluoride diethyl etherate; lithium diethylamide; tetrabutyl ammonium fluoride; iodine; acetic acid; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III);
DOI:10.1021/jo970380f