(1S,2S,3S,4S,5S)-1,2-di-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohexane-1,2,3,4,5-pentol

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Chemical Name:(1S,2S,3S,4S,5S)-1,2-di-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohexane-1,2,3,4,5-pentol
CAS No.:374687-90-8
Molecular Formula:C₃₂H₃₆O₈
Molecular Weight:548.633
Hs Code.:

Synonyms:(1S,2S,3S,4S,5S)-1,2-di-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohexane-1,2,3,4,5-pentol

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Chemical Property of (1S,2S,3S,4S,5S)-1,2-di-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohexane-1,2,3,4,5-pentol

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Technology Process of (1S,2S,3S,4S,5S)-1,2-di-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohexane-1,2,3,4,5-pentol

There total 16 articles about (1S,2S,3S,4S,5S)-1,2-di-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohexane-1,2,3,4,5-pentol 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: 96.0%

: 108-24-7
acetic anhydride

: 374688-00-3
(1S,2S,4S,5S,6R)-5,6-Bis-benzyloxy-4-benzyloxymethyl-cyclohexane-1,2,4-triol

: 374687-90-8
(1S,2S,3S,4S,5S)-1,2-di-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohexane-1,2,3,4,5-pentol

Guidance literature:: With pyridine; dmap; In dichloromethane; at 20 ℃; for 12h;
DOI:10.1021/jo010202t

Reference yield:

: 77-95-2
D-(-)-quinic acid

: 374687-90-8
(1S,2S,3S,4S,5S)-1,2-di-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohexane-1,2,3,4,5-pentol

Guidance literature:: Multi-step reaction with 15 steps

1.1: 94 percent / conc. H₃PO₄ / 12 h / 180 °C

2.1: 98 percent Turnov_. / NaOMe / 2.5 h / 0 °C

3.1: 86 percent / 3 Angstroem molecular sieves; pyridinium dichromate / CH₂Cl₂; acetic acid / 24 h / 20 °C

4.1: 99 percent / POCl₃; pyridine / 0 - 20 °C

5.1: 93 percent / DIBALH / toluene / 1 h / -40 - 0 °C

6.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

6.2: 98 percent / nBu₄NI / tetrahydrofuran / 12 h / Heating

7.1: 92 percent / NMO; OsO₄ / acetone; H₂O / 48 h / 20 °C

8.1: NaH / tetrahydrofuran / 1 h / 0 °C

8.2: 98 percent / nBu₄NI / tetrahydrofuran / 3 h / 20 °C

9.1: pyridine; DMAP / 24 h

10.1: 100 percent / TFA; H₂O / CH₂Cl₂ / 24 h / 20 °C

11.1: toluene / 4 h / Heating

12.1: 1.48 g / P(OMe)3 / 24 h / Heating

13.1: 81 percent / NaIO₄; RuCl₃*3H₂O / ethyl acetate; acetonitrile; H₂O / 0.05 h / 0 °C

14.1: 92 percent / K₂CO₃ / methanol / 3 h / 20 °C

15.1: 96 percent / pyridine; DMAP / CH₂Cl₂ / 12 h / 20 °C

With pyridine; dmap; ruthenium trichloride; sodium periodate; osmium(VIII) oxide; dipyridinium dichromate; N-methyl-2-indolinone; phosphoric acid; 3 A molecular sieve; water; sodium methylate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; trifluoroacetic acid; phosphorous acid trimethyl ester; trichlorophosphate; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; ethyl acetate; acetone; toluene; acetonitrile;
DOI:10.1021/jo010202t

Reference yield:

: 100-39-0
benzyl bromide

: 374687-90-8
(1S,2S,3S,4S,5S)-1,2-di-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)cyclohexane-1,2,3,4,5-pentol

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaH / tetrahydrofuran / 0.5 h / 0 °C

1.2: 98 percent / nBu₄NI / tetrahydrofuran / 12 h / Heating

2.1: 92 percent / NMO; OsO₄ / acetone; H₂O / 48 h / 20 °C

3.1: NaH / tetrahydrofuran / 1 h / 0 °C

3.2: 98 percent / nBu₄NI / tetrahydrofuran / 3 h / 20 °C

4.1: pyridine; DMAP / 24 h

5.1: 100 percent / TFA; H₂O / CH₂Cl₂ / 24 h / 20 °C

6.1: toluene / 4 h / Heating

7.1: 1.48 g / P(OMe)3 / 24 h / Heating

8.1: 81 percent / NaIO₄; RuCl₃*3H₂O / ethyl acetate; acetonitrile; H₂O / 0.05 h / 0 °C

9.1: 92 percent / K₂CO₃ / methanol / 3 h / 20 °C

10.1: 96 percent / pyridine; DMAP / CH₂Cl₂ / 12 h / 20 °C

With pyridine; dmap; ruthenium trichloride; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; water; sodium hydride; potassium carbonate; trifluoroacetic acid; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone; toluene; acetonitrile;
DOI:10.1021/jo010202t