(2S,3S,5R)-5-{[(tert-butyl)(dimethyl)silyl]oxy}-2-hydroxy-3-(methoxymethoxy)hexyl 4-methylbenzenesulfonate

Base Information

Chemical Name:(2S,3S,5R)-5-{[(tert-butyl)(dimethyl)silyl]oxy}-2-hydroxy-3-(methoxymethoxy)hexyl 4-methylbenzenesulfonate
CAS No.:1621085-63-9
Molecular Formula:C₂₁H₃₈O₇SSi
Molecular Weight:462.68
Hs Code.:

Synonyms:(2S,3S,5R)-5-{[(tert-butyl)(dimethyl)silyl]oxy}-2-hydroxy-3-(methoxymethoxy)hexyl 4-methylbenzenesulfonate

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Chemical Property of (2S,3S,5R)-5-{[(tert-butyl)(dimethyl)silyl]oxy}-2-hydroxy-3-(methoxymethoxy)hexyl 4-methylbenzenesulfonate

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Technology Process of (2S,3S,5R)-5-{[(tert-butyl)(dimethyl)silyl]oxy}-2-hydroxy-3-(methoxymethoxy)hexyl 4-methylbenzenesulfonate

There total 5 articles about (2S,3S,5R)-5-{[(tert-butyl)(dimethyl)silyl]oxy}-2-hydroxy-3-(methoxymethoxy)hexyl 4-methylbenzenesulfonate 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: 95.0%

: 1621085-52-6
(2S,3S,5R)-5-{[(tert-Butyl)(dimethyl)silyl]oxy}-3-(methoxymethoxy)hexane-1,2-diol

: 98-59-9
p-toluenesulfonyl chloride

: 1621085-63-9
(2S,3S,5R)-5-{[(tert-butyl)(dimethyl)silyl]oxy}-2-hydroxy-3-(methoxymethoxy)hexyl 4-methylbenzenesulfonate

Guidance literature:: (2S,3S,5R)-5-{[(tert-Butyl)(dimethyl)silyl]oxy}-3-(methoxymethoxy)hexane-1,2-diol; With di(n-butyl)tin oxide; triethylamine; In dichloromethane; at 0 ℃; for 0.25h;

p-toluenesulfonyl chloride; In dichloromethane; at 0 - 20 ℃; for 3h;
DOI:10.1002/hlca.201300203

Reference yield:

: 1621085-54-8
C₁₄H₃₀O₄Si

: 1621085-63-9
(2S,3S,5R)-5-{[(tert-butyl)(dimethyl)silyl]oxy}-2-hydroxy-3-(methoxymethoxy)hexyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 2 steps

1.1: Nitrosobenzene; L-proline / acetonitrile / 12 h / -20 °C

1.2: 0.5 h

1.3: 10 h / 0 °C

2.1: triethylamine; di(n-butyl)tin oxide / dichloromethane / 0.25 h / 0 °C

2.2: 3 h / 0 - 20 °C

With di(n-butyl)tin oxide; triethylamine; Nitrosobenzene; L-proline; In dichloromethane; acetonitrile;
DOI:10.1002/hlca.201300203

Reference yield:

: 1621085-57-1
(2R,4R)-4-(methoxymethoxy)hept-6-en-2-ol

: 1621085-63-9
(2S,3S,5R)-5-{[(tert-butyl)(dimethyl)silyl]oxy}-2-hydroxy-3-(methoxymethoxy)hexyl 4-methylbenzenesulfonate

Guidance literature:: Multi-step reaction with 4 steps

1.1: dmap; 1H-imidazole / dichloromethane / 4 h / 0 °C

2.1: ozone / dichloromethane / -78 °C

2.2: 2 h / 0 °C / Inert atmosphere

3.1: Nitrosobenzene; L-proline / acetonitrile / 12 h / -20 °C

3.2: 0.5 h

3.3: 10 h / 0 °C

4.1: triethylamine; di(n-butyl)tin oxide / dichloromethane / 0.25 h / 0 °C

4.2: 3 h / 0 - 20 °C

With 1H-imidazole; dmap; di(n-butyl)tin oxide; ozone; triethylamine; Nitrosobenzene; L-proline; In dichloromethane; acetonitrile;
DOI:10.1002/hlca.201300203