2R-(3S-{3S-[2R,3R-bis-benzyloxy-3R-methyl-5R-(triisopropylsilanyloxy)-tetrahydropyran-4R-yloxy]-hex-4Z-enyl}-3S-methyloxiranylmethyl)-6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxytetrahydropyran-3R-ol

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Chemical Name:2R-(3S-{3S-[2R,3R-bis-benzyloxy-3R-methyl-5R-(triisopropylsilanyloxy)-tetrahydropyran-4R-yloxy]-hex-4Z-enyl}-3S-methyloxiranylmethyl)-6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxytetrahydropyran-3R-ol
CAS No.:569660-79-3
Molecular Formula:C₅₃H₈₄O₁₂Si
Molecular Weight:941.328
Hs Code.:

2R-(3S-{3S-[2R,3R-bis-benzyloxy-3R-methyl-5R-(triisopropylsilanyloxy)-tetrahydropyran-4R-yloxy]-hex-4Z-enyl}-3S-methyloxiranylmethyl)-6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxytetrahydropyran-3R-ol

Synonyms:2R-(3S-{3S-[2R,3R-bis-benzyloxy-3R-methyl-5R-(triisopropylsilanyloxy)-tetrahydropyran-4R-yloxy]-hex-4Z-enyl}-3S-methyloxiranylmethyl)-6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxytetrahydropyran-3R-ol

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Chemical Property of 2R-(3S-{3S-[2R,3R-bis-benzyloxy-3R-methyl-5R-(triisopropylsilanyloxy)-tetrahydropyran-4R-yloxy]-hex-4Z-enyl}-3S-methyloxiranylmethyl)-6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxytetrahydropyran-3R-ol

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Technology Process of 2R-(3S-{3S-[2R,3R-bis-benzyloxy-3R-methyl-5R-(triisopropylsilanyloxy)-tetrahydropyran-4R-yloxy]-hex-4Z-enyl}-3S-methyloxiranylmethyl)-6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxytetrahydropyran-3R-ol

There total 10 articles about 2R-(3S-{3S-[2R,3R-bis-benzyloxy-3R-methyl-5R-(triisopropylsilanyloxy)-tetrahydropyran-4R-yloxy]-hex-4Z-enyl}-3S-methyloxiranylmethyl)-6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxytetrahydropyran-3R-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: 94.0%

: 569661-75-2
5-[6R-(3-{3S-[2R,3R-bis-benzyloxy-3R-methyl-5R-(triisopropylsilanyloxy)-tetrahydropyran-4R-yloxy]-hex-4Z-enyl}-3S-methyloxiranylmethyl)-4S-methoxymethyoxy-5R-(triethylsilanyloxy)-tetrahydropyran-2R-ylmethyl]-2,2-dimethyl-[1,3]dioxane

: 569660-79-3
2R-(3S-{3S-[2R,3R-bis-benzyloxy-3R-methyl-5R-(triisopropylsilanyloxy)-tetrahydropyran-4R-yloxy]-hex-4Z-enyl}-3S-methyloxiranylmethyl)-6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxytetrahydropyran-3R-ol

Guidance literature:: With pyridine; hydrogen fluoride; In acetonitrile; at 25 ℃; for 7h;
DOI:10.1021/ja029225v

Reference yield: 72.0%

: 1530-32-1
ethyltriphenylphosphonium bromide

: 569661-73-0
2S-[2R,3R-bisbenzyloxy-3R-methyl-5R-(triisopropylsilanyloxy)-tetrahydropyran-4-yloxy]-4-{3S-[6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxy-3R-(triethylsilanoxy)-tetrahydropyran-2R-ylmethyl]-2S-methyl-oxiranyl}butyraldehyde

: 569660-79-3
2R-(3S-{3S-[2R,3R-bis-benzyloxy-3R-methyl-5R-(triisopropylsilanyloxy)-tetrahydropyran-4R-yloxy]-hex-4Z-enyl}-3S-methyloxiranylmethyl)-6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxytetrahydropyran-3R-ol

: 569661-75-2
5-[6R-(3-{3S-[2R,3R-bis-benzyloxy-3R-methyl-5R-(triisopropylsilanyloxy)-tetrahydropyran-4R-yloxy]-hex-4Z-enyl}-3S-methyloxiranylmethyl)-4S-methoxymethyoxy-5R-(triethylsilanyloxy)-tetrahydropyran-2R-ylmethyl]-2,2-dimethyl-[1,3]dioxane

Guidance literature:: ethyltriphenylphosphonium bromide; With sodium hexamethyldisilazane; In tetrahydrofuran; at 0 ℃; for 0.5h;

2S-[2R,3R-bisbenzyloxy-3R-methyl-5R-(triisopropylsilanyloxy)-tetrahydropyran-4-yloxy]-4-{3S-[6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxy-3R-(triethylsilanoxy)-tetrahydropyran-2R-ylmethyl]-2S-methyl-oxiranyl}butyraldehyde; With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; In tetrahydrofuran; at -78 - 20 ℃; for 1.5h;
DOI:10.1021/ja029225v

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 569660-79-3
2R-(3S-{3S-[2R,3R-bis-benzyloxy-3R-methyl-5R-(triisopropylsilanyloxy)-tetrahydropyran-4R-yloxy]-hex-4Z-enyl}-3S-methyloxiranylmethyl)-6R-(2,2-dimethyl-[1,3]dioxan-5-ylmethyl)-4S-methoxymethoxytetrahydropyran-3R-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 92 percent / 2,6-lutidine / various solvent(s) / 0.25 h / -78 °C

2.1: CH₂Cl₂; methanol / 25 h / -30 °C

3.1: LiAlH₄ / tetrahydrofuran / 0.75 h / -78 °C

4.1: oxalyl chloride; dimethylsulfoxide; diisopropylethylamine / CH₂Cl₂ / -78 - 0 °C

5.1: sodium hexamethyldisilazide / tetrahydrofuran / 0.5 h / 0 °C

5.2: 18 percent / DMPU / tetrahydrofuran / 1.5 h / -78 - 20 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; oxalyl dichloride; sodium hexamethyldisilazane; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; 4.1: Swern oxidation;
DOI:10.1021/ja029225v