[2R,3R,4S,6S,1'R]-3,4:1',2'-diisopropylidene-6-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxy-2-(1,2-dihydroxyethyl)tetrahydro-2H-pyran

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Chemical Name:[2R,3R,4S,6S,1'R]-3,4:1',2'-diisopropylidene-6-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxy-2-(1,2-dihydroxyethyl)tetrahydro-2H-pyran
CAS No.:256343-21-2
Molecular Formula:C₃₀H₄₂O₆Si
Molecular Weight:526.745
Hs Code.:

Synonyms:[2R,3R,4S,6S,1'R]-3,4:1',2'-diisopropylidene-6-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxy-2-(1,2-dihydroxyethyl)tetrahydro-2H-pyran

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Chemical Property of [2R,3R,4S,6S,1'R]-3,4:1',2'-diisopropylidene-6-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxy-2-(1,2-dihydroxyethyl)tetrahydro-2H-pyran

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Technology Process of [2R,3R,4S,6S,1'R]-3,4:1',2'-diisopropylidene-6-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxy-2-(1,2-dihydroxyethyl)tetrahydro-2H-pyran

There total 6 articles about [2R,3R,4S,6S,1'R]-3,4:1',2'-diisopropylidene-6-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxy-2-(1,2-dihydroxyethyl)tetrahydro-2H-pyran 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: 55.0%

: 67-64-1
acetone

: 171411-71-5
[4S,6S,1'R]-2-(tert-butyldiphenylsilyloxymethyl)-6-(1,2-dihydroxyethyl)-3,6-dihydro-2H-pyran

: [2R,3S,4R,6S,1'R]-3,4:1',2'-diisopropylidene-6-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxy-2-(1,2-dihydroxyethyl)tetrahydro-2H-pyran

: 256343-21-2
[2R,3R,4S,6S,1'R]-3,4:1',2'-diisopropylidene-6-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxy-2-(1,2-dihydroxyethyl)tetrahydro-2H-pyran

Guidance literature:: [4S,6S,1'R]-2-(tert-butyldiphenylsilyloxymethyl)-6-(1,2-dihydroxyethyl)-3,6-dihydro-2H-pyran; With osmium(VIII) oxide; N-morpholine-N-oxide; In water; acetone; at 25 ℃; for 0.5h;

acetone; With sulfuric acid; copper(II) sulfate; at 25 ℃; for 0.25h;
DOI:10.1016/S0040-4020(99)00834-0

Reference yield:

: 256343-23-4
(3aS,5S,7S,7aS)-7-Benzenesulfonyl-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furo[3,2-b]pyran-3-one

: 256343-21-2
[2R,3R,4S,6S,1'R]-3,4:1',2'-diisopropylidene-6-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxy-2-(1,2-dihydroxyethyl)tetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 3 steps

1.1: 74 percent / NaBH₄ / methanol / 1 h / 0 °C

2.1: 70 percent / 6 percent Na(Hg) / methanol / 1 h / 0 °C

3.1: OsO₄; N-morpholine-N-oxide / acetone; H₂O / 0.5 h / 25 °C

3.2: 21 percent / conc. H₂SO₄; CuSO₄ / 0.25 h / 25 °C

With sodium tetrahydroborate; osmium(VIII) oxide; sodium amalgam; N-morpholine-N-oxide; In methanol; water; acetone; 1.1: Reduction / 2.1: Ring cleavage / 3.1: Oxidation / 3.2: Cycloaddition;
DOI:10.1016/S0040-4020(99)00834-0

Reference yield:

: 171411-65-7
[2S,4S]-2-(tert-butyldiphenylsilyloxymethyl)-4-phenylsulfonyl-3,4-dihydro-2H-pyran

: 256343-21-2
[2R,3R,4S,6S,1'R]-3,4:1',2'-diisopropylidene-6-(tert-butyldiphenylsilyloxymethyl)-3,4-dihydroxy-2-(1,2-dihydroxyethyl)tetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 6 steps

1.1: m-CPBA / diethyl ether; H₂O / 16 h

1.2: 471 mg / (n-Bu)3P / CH₂Cl₂ / 0.5 h / 25 °C

2.1: 86 percent / NaOH; Aliquat 336 / CH₂Cl₂; H₂O / 0.25 h / 25 °C

3.1: AgOTf; 4A molecular sieves; DBU / CH₂Cl₂ / 25 °C

3.2: 79 percent / ozone; triphenylphosphine / CH₂Cl₂ / -78 - 25 °C

4.1: 74 percent / NaBH₄ / methanol / 1 h / 0 °C

5.1: 70 percent / 6 percent Na(Hg) / methanol / 1 h / 0 °C

6.1: OsO₄; N-morpholine-N-oxide / acetone; H₂O / 0.5 h / 25 °C

6.2: 21 percent / conc. H₂SO₄; CuSO₄ / 0.25 h / 25 °C

With sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; sodium amalgam; N-morpholine-N-oxide; 4 A molecular sieve; silver trifluoromethanesulfonate; Aliquat 336; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; In methanol; diethyl ether; dichloromethane; water; acetone; 1.1: Oxidation / 1.2: Substitution / 2.1: Etherification / 3.1: Cyclization / 3.2: Oxidation / 4.1: Reduction / 5.1: Ring cleavage / 6.1: Oxidation / 6.2: Cycloaddition;
DOI:10.1016/S0040-4020(99)00834-0