(8aR,9R,10S,11R,12aS,Z)-9,10-bis(benzyloxy)-11-(benzyloxymethyl)-8a,9,10,11-tetrahydro-2H-pyrano[2,3-b][1,6]dioxecin-7(5H,8H,12aH)one

Base Information

Chemical Name:(8aR,9R,10S,11R,12aS,Z)-9,10-bis(benzyloxy)-11-(benzyloxymethyl)-8a,9,10,11-tetrahydro-2H-pyrano[2,3-b][1,6]dioxecin-7(5H,8H,12aH)one
CAS No.:1124226-20-5
Molecular Formula:C₃₃H₃₆O₇
Molecular Weight:544.645
Hs Code.:

Synonyms:(8aR,9R,10S,11R,12aS,Z)-9,10-bis(benzyloxy)-11-(benzyloxymethyl)-8a,9,10,11-tetrahydro-2H-pyrano[2,3-b][1,6]dioxecin-7(5H,8H,12aH)one

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Chemical Property of (8aR,9R,10S,11R,12aS,Z)-9,10-bis(benzyloxy)-11-(benzyloxymethyl)-8a,9,10,11-tetrahydro-2H-pyrano[2,3-b][1,6]dioxecin-7(5H,8H,12aH)one

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Technology Process of (8aR,9R,10S,11R,12aS,Z)-9,10-bis(benzyloxy)-11-(benzyloxymethyl)-8a,9,10,11-tetrahydro-2H-pyrano[2,3-b][1,6]dioxecin-7(5H,8H,12aH)one

There total 3 articles about (8aR,9R,10S,11R,12aS,Z)-9,10-bis(benzyloxy)-11-(benzyloxymethyl)-8a,9,10,11-tetrahydro-2H-pyrano[2,3-b][1,6]dioxecin-7(5H,8H,12aH)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: 75.0%

: 1124225-89-3
allyl 3,4,6-tri-O-benzyl-2-deoxy-2-[(allyloxycarbonyl)methyl]-α-D-glucopyranoside

: 1124226-20-5
(8aR,9R,10S,11R,12aS,Z)-9,10-bis(benzyloxy)-11-(benzyloxymethyl)-8a,9,10,11-tetrahydro-2H-pyrano[2,3-b][1,6]dioxecin-7(5H,8H,12aH)one

Guidance literature:: With Grubbs catalyst first generation; In dichloromethane; at 20 ℃; for 48h; Inert atmosphere;
DOI:10.1016/j.tet.2011.01.069

Reference yield:

: 946512-97-6
methyl 3,4,6-tri-O-benzyl-2-deoxy-2-C-[(bis-methoxycarbonyl)methyl]-β-D-glucopyranoside

: 1124226-20-5
(8aR,9R,10S,11R,12aS,Z)-9,10-bis(benzyloxy)-11-(benzyloxymethyl)-8a,9,10,11-tetrahydro-2H-pyrano[2,3-b][1,6]dioxecin-7(5H,8H,12aH)one

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium hydroxide monohydrate / methanol; water / 1 h / Inert atmosphere; Reflux

2.1: acetic acid / toluene / 1 h / 110 °C / pH 3 - 4 / Inert atmosphere

3.1: calcium sulfate; scandium tris(trifluoromethanesulfonate) / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

3.2: 0 - 20 °C / Inert atmosphere

4.1: Grubbs catalyst first generation / dichloromethane / 48 h / 20 °C / Inert atmosphere

With Grubbs catalyst first generation; calcium sulfate; lithium hydroxide monohydrate; acetic acid; scandium tris(trifluoromethanesulfonate); In methanol; dichloromethane; water; toluene;
DOI:10.1016/j.tet.2011.01.069

Reference yield:

: 1124225-72-4
(3aR,4R,5S,6R,7aR)-4,5-bis(benzyloxy)-6-benzyloxymethyl-2-oxohexahydrofuro[2,3-b]pyran

: 1124226-20-5
(8aR,9R,10S,11R,12aS,Z)-9,10-bis(benzyloxy)-11-(benzyloxymethyl)-8a,9,10,11-tetrahydro-2H-pyrano[2,3-b][1,6]dioxecin-7(5H,8H,12aH)one

Guidance literature:: Multi-step reaction with 2 steps

1.1: calcium sulfate; scandium tris(trifluoromethanesulfonate) / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: Grubbs catalyst first generation / dichloromethane / 48 h / 20 °C / Inert atmosphere

With Grubbs catalyst first generation; calcium sulfate; scandium tris(trifluoromethanesulfonate); In dichloromethane;
DOI:10.1016/j.tet.2011.01.069