1-[(2R,3R,4R,5R,6R)-6-[(1R,2R)-2-Hydroxy-1-(4-methoxy-benzyloxy)-propyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-propan-2-one

Base Information

Chemical Name:1-[(2R,3R,4R,5R,6R)-6-[(1R,2R)-2-Hydroxy-1-(4-methoxy-benzyloxy)-propyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-propan-2-one
CAS No.:392692-54-5
Molecular Formula:C₃₆H₄₆O₉
Molecular Weight:622.756
Hs Code.:

Synonyms:1-[(2R,3R,4R,5R,6R)-6-[(1R,2R)-2-Hydroxy-1-(4-methoxy-benzyloxy)-propyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-propan-2-one

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Chemical Property of 1-[(2R,3R,4R,5R,6R)-6-[(1R,2R)-2-Hydroxy-1-(4-methoxy-benzyloxy)-propyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-propan-2-one

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Technology Process of 1-[(2R,3R,4R,5R,6R)-6-[(1R,2R)-2-Hydroxy-1-(4-methoxy-benzyloxy)-propyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-propan-2-one

There total 19 articles about 1-[(2R,3R,4R,5R,6R)-6-[(1R,2R)-2-Hydroxy-1-(4-methoxy-benzyloxy)-propyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-propan-2-one 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: 86.0%

: 392692-56-7
(3E,5R,6R,7R)-5,6-bis-(p-methoxybenzyloxy)-7-[5-(R)-(p-methoxybenzyloxy)-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-oct-3-en-2-one

: 392692-54-5
1-[(2R,3R,4R,5R,6R)-6-[(1R,2R)-2-Hydroxy-1-(4-methoxy-benzyloxy)-propyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-propan-2-one

Guidance literature:: (3E,5R,6R,7R)-5,6-bis-(p-methoxybenzyloxy)-7-[5-(R)-(p-methoxybenzyloxy)-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-oct-3-en-2-one; With acetic acid; In tetrahydrofuran; water; at 20 ℃; for 48h;

With potassium hydroxide; In methanol; at 20 ℃; for 24h;
DOI:10.1002/1521-3773(20011105)40:21<4055::AID-ANIE4055>3.0.CO;2-H

Reference yield:

: 862509-84-0
(4R,5R,6R)-5-benzyloxy-4-[1-hydroxy-prop-2-(R)-yl]-2,2,6-trimethyl-1,3-dioxane

: 392692-54-5
1-[(2R,3R,4R,5R,6R)-6-[(1R,2R)-2-Hydroxy-1-(4-methoxy-benzyloxy)-propyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-propan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

2.1: LiCl; i-PrNEt₂ / acetonitrile / 16 h / 20 °C

3.1: enriched AD-mix-β; MeSO3NH2 / 2-methyl-propan-2-ol; H2O / 8 h / 20 °C

4.1: H₂; NaHCO₃ / Pd(OH)2/C / methanol / 20 h / 20 °C

5.1: Ph₃CBF₄ / tetrahydrofuran / 2 h / 0 °C

6.1: DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

6.2: Ba(OH)2 / tetrahydrofuran; H₂O / 16 h / 20 °C

7.1: AcOH / tetrahydrofuran; H₂O / 48 h / 20 °C

7.2: 86 percent / KOH / methanol / 24 h / 20 °C

With sulfamic acid methyl ester; N,N-diethyl-N-isopropylamine; enriched AD-mix-β; hydrogen; trityl tetrafluoroborate; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; lithium chloride; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; tert-butyl alcohol; 1.1: Dess-Martin oxidation / 2.1: Horner-Wadsworth-Emmons olefination / 3.1: Sharpless dihydroxylation / 6.2: Horner-Wadsworth-Emmons olefination / 7.1: hetero-Michael cyclization;
DOI:10.1002/1521-3773(20011105)40:21<4055::AID-ANIE4055>3.0.CO;2-H

Reference yield:

: 194934-58-2
(S)-2-[5-(R)-benzyloxy-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-propionaldehyde

: 392692-54-5
1-[(2R,3R,4R,5R,6R)-6-[(1R,2R)-2-Hydroxy-1-(4-methoxy-benzyloxy)-propyl]-3,4-bis-(4-methoxy-benzyloxy)-5-methyl-tetrahydro-pyran-2-yl]-propan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: LiCl; i-PrNEt₂ / acetonitrile / 16 h / 20 °C

2.1: enriched AD-mix-β; MeSO3NH2 / 2-methyl-propan-2-ol; H2O / 8 h / 20 °C

3.1: H₂; NaHCO₃ / Pd(OH)2/C / methanol / 20 h / 20 °C

4.1: Ph₃CBF₄ / tetrahydrofuran / 2 h / 0 °C

5.1: DIBAL-H / CH₂Cl₂ / 0.5 h / -78 °C

5.2: Ba(OH)2 / tetrahydrofuran; H₂O / 16 h / 20 °C

6.1: AcOH / tetrahydrofuran; H₂O / 48 h / 20 °C

6.2: 86 percent / KOH / methanol / 24 h / 20 °C

With sulfamic acid methyl ester; N,N-diethyl-N-isopropylamine; enriched AD-mix-β; hydrogen; trityl tetrafluoroborate; diisobutylaluminium hydride; sodium hydrogencarbonate; acetic acid; lithium chloride; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; tert-butyl alcohol; 1.1: Horner-Wadsworth-Emmons olefination / 2.1: Sharpless dihydroxylation / 5.2: Horner-Wadsworth-Emmons olefination / 6.1: hetero-Michael cyclization;
DOI:10.1002/1521-3773(20011105)40:21<4055::AID-ANIE4055>3.0.CO;2-H