(3R,4S,5S)-5-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)-1-cyclohexene-3,4,5-triol

Base Information

Chemical Name:(3R,4S,5S)-5-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)-1-cyclohexene-3,4,5-triol
CAS No.:374687-88-4
Molecular Formula:C₃₀H₃₂O₅
Molecular Weight:472.581
Hs Code.:

Synonyms:(3R,4S,5S)-5-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)-1-cyclohexene-3,4,5-triol

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Chemical Property of (3R,4S,5S)-5-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)-1-cyclohexene-3,4,5-triol

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Technology Process of (3R,4S,5S)-5-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)-1-cyclohexene-3,4,5-triol

There total 13 articles about (3R,4S,5S)-5-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)-1-cyclohexene-3,4,5-triol 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:

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

: 374687-88-4
(3R,4S,5S)-5-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)-1-cyclohexene-3,4,5-triol

Guidance literature:: Multi-step reaction with 12 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

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

Reference yield:

: 100-39-0
benzyl bromide

: 374687-88-4
(3R,4S,5S)-5-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)-1-cyclohexene-3,4,5-triol

Guidance literature:: Multi-step reaction with 7 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

With pyridine; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; water; sodium hydride; trifluoroacetic acid; phosphorous acid trimethyl ester; In tetrahydrofuran; dichloromethane; water; acetone; toluene;
DOI:10.1021/jo010202t

Reference yield:

: 374687-81-7
methyl 4,5-O-ethylpropylidene-3-dehydro-4-epi-shikimate

: 374687-88-4
(3R,4S,5S)-5-O-acetyl-3,4-di-O-benzyl-5-(benzyloxymethyl)-1-cyclohexene-3,4,5-triol

Guidance literature:: Multi-step reaction with 8 steps

1.1: 93 percent / DIBALH / toluene / 1 h / -40 - 0 °C

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

2.2: 98 percent / nBu₄NI / tetrahydrofuran / 12 h / Heating

3.1: 92 percent / NMO; OsO₄ / acetone; H₂O / 48 h / 20 °C

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

4.2: 98 percent / nBu₄NI / tetrahydrofuran / 3 h / 20 °C

5.1: pyridine; DMAP / 24 h

6.1: 100 percent / TFA; H₂O / CH₂Cl₂ / 24 h / 20 °C

7.1: toluene / 4 h / Heating

8.1: 1.48 g / P(OMe)3 / 24 h / Heating

With pyridine; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; water; sodium hydride; diisobutylaluminium hydride; trifluoroacetic acid; phosphorous acid trimethyl ester; In tetrahydrofuran; dichloromethane; water; acetone; toluene;
DOI:10.1021/jo010202t