methyl (2S,3R,4R)-2,3-bis-(p-methoxybenzyloxy)-4-[5-(R)-(p-methoxybenzyloxy)-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-pentanoate

Base Information

Chemical Name:methyl (2S,3R,4R)-2,3-bis-(p-methoxybenzyloxy)-4-[5-(R)-(p-methoxybenzyloxy)-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-pentanoate
CAS No.:392692-55-6
Molecular Formula:C₃₇H₄₈O₁₀
Molecular Weight:652.782
Hs Code.:

Synonyms:methyl (2S,3R,4R)-2,3-bis-(p-methoxybenzyloxy)-4-[5-(R)-(p-methoxybenzyloxy)-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-pentanoate

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Chemical Property of methyl (2S,3R,4R)-2,3-bis-(p-methoxybenzyloxy)-4-[5-(R)-(p-methoxybenzyloxy)-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-pentanoate

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Technology Process of methyl (2S,3R,4R)-2,3-bis-(p-methoxybenzyloxy)-4-[5-(R)-(p-methoxybenzyloxy)-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-pentanoate

There total 9 articles about methyl (2S,3R,4R)-2,3-bis-(p-methoxybenzyloxy)-4-[5-(R)-(p-methoxybenzyloxy)-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-pentanoate 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: 97.0%

: 89238-99-3
O-(4-methoxybenzyl)-trichloroacetimidate

: 862509-74-8
methyl (2S,3R,4R)-2,3-dihydroxy-4-[5-(R)-hydroxy-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-pentanoate

: 392692-55-6
methyl (2S,3R,4R)-2,3-bis-(p-methoxybenzyloxy)-4-[5-(R)-(p-methoxybenzyloxy)-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-pentanoate

Guidance literature:: With trityl tetrafluoroborate; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1039/b504149j

Reference yield:

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

: 392692-55-6
methyl (2S,3R,4R)-2,3-bis-(p-methoxybenzyloxy)-4-[5-(R)-(p-methoxybenzyloxy)-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-pentanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 80 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

2.1: LiCl; i-Pr₂NEt / acetonitrile / 0.17 h / 20 °C

2.2: 96 percent / acetonitrile / 16 h / 20 °C

3.1: 98 percent / aq. AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol / 16 h / 20 °C

4.1: 100 percent / NaHCO₃; H₂ / Pd(OH)2/C / methanol / 20 h / 20 °C

5.1: 97 percent / Ph₃CBF₄ / tetrahydrofuran / 0.5 h / 0 °C

With methanesulfonamide; AD-mix-β; hydrogen; trityl tetrafluoroborate; sodium hydrogencarbonate; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium dihydroxide; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; tert-butyl alcohol; 2.2: Horner-Wadsworth-Emmons chain extension / 3.1: Sharpless asymmetric dihydroxylation;
DOI:10.1039/b504149j

Reference yield:

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

: 392692-55-6
methyl (2S,3R,4R)-2,3-bis-(p-methoxybenzyloxy)-4-[5-(R)-(p-methoxybenzyloxy)-2,2,6-(6R)-trimethyl-1,3-dioxan-4-(R)-yl]-pentanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: LiCl; i-Pr₂NEt / acetonitrile / 0.17 h / 20 °C

1.2: 96 percent / acetonitrile / 16 h / 20 °C

2.1: 98 percent / aq. AD-mix-β; MeSO2NH2 / 2-methyl-propan-2-ol / 16 h / 20 °C

3.1: 100 percent / NaHCO₃; H₂ / Pd(OH)2/C / methanol / 20 h / 20 °C

4.1: 97 percent / Ph₃CBF₄ / tetrahydrofuran / 0.5 h / 0 °C

With methanesulfonamide; AD-mix-β; hydrogen; trityl tetrafluoroborate; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium dihydroxide; In tetrahydrofuran; methanol; acetonitrile; tert-butyl alcohol; 1.2: Horner-Wadsworth-Emmons chain extension / 2.1: Sharpless asymmetric dihydroxylation;
DOI:10.1039/b504149j