(2S,4RS,6S)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane

Base Information

Chemical Name:(2S,4RS,6S)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane
CAS No.:299430-05-0
Molecular Formula:C₂₆H₄₆O₅SSi
Molecular Weight:498.8
Hs Code.:

Synonyms:(2S,4RS,6S)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane

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Chemical Property of (2S,4RS,6S)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane

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Technology Process of (2S,4RS,6S)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane

There total 7 articles about (2S,4RS,6S)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane 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: 88.0%

: 299430-04-9
(S)-2-methyl-4-phenylsulfonyl-1-tetrahydropyranyloxybutane

: 105859-46-9
(2R)-(tert-butyldimethyl)-(3-iodo-2-methylpropoxy)silane

: 299430-05-0
(2S,4RS,6S)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane

Guidance literature:: (S)-2-methyl-4-phenylsulfonyl-1-tetrahydropyranyloxybutane; With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at -30 ℃; for 1h;

(2R)-(tert-butyldimethyl)-(3-iodo-2-methylpropoxy)silane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; at 20 ℃; for 10h;
DOI:10.1002/1099-0690(200008)2000:15<2745::AID-EJOC2745>3.0.CO;2-I

Reference yield:

: 3112-85-4
methylphenylsulfonate

: 299430-05-0
(2S,4RS,6S)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane

Guidance literature:: Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 0.5 h / -30 °C

1.2: 74 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 9 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1 h / -30 °C

2.2: 88 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 10 h / 20 °C

With n-butyllithium; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; 1.1: Metallation / 1.2: Alkylation / 2.1: Metallation / 2.2: Alkylation;
DOI:10.1002/1099-0690(200008)2000:15<2745::AID-EJOC2745>3.0.CO;2-I

Reference yield:

: 105859-45-8
(S)-3-(tert-butyldimethylsilyloxy)-2-methylpropan-1-ol

: 299430-05-0
(2S,4RS,6S)-1-tert-butyldimethylsilyloxy-2,6-dimethyl-4-phenylsulfonyl-7-tetrahydropyranyloxyheptane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 100 percent / pyridine / 12 h / 0 °C

2.1: 94 percent / NaI; NaHCO₃ / acetone / 4 h / Heating

3.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1 h / -30 °C

3.2: 88 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 10 h / 20 °C

With n-butyllithium; sodium hydrogencarbonate; sodium iodide; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; acetone; 1.1: Tosylation / 2.1: Substitution / 3.1: Metallation / 3.2: Alkylation;
DOI:10.1002/1099-0690(200008)2000:15<2745::AID-EJOC2745>3.0.CO;2-I