(1S,3R,4S,5R)-4-(benzyloxy)-3-(benzyloxymethyl)-2,8-dioxabicyclo[3.3.1]non-6-ene

Base Information

Chemical Name:(1S,3R,4S,5R)-4-(benzyloxy)-3-(benzyloxymethyl)-2,8-dioxabicyclo[3.3.1]non-6-ene
CAS No.:1581705-02-3
Molecular Formula:C₂₂H₂₄O₄
Molecular Weight:352.43
Hs Code.:

Synonyms:(1S,3R,4S,5R)-4-(benzyloxy)-3-(benzyloxymethyl)-2,8-dioxabicyclo[3.3.1]non-6-ene

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Chemical Property of (1S,3R,4S,5R)-4-(benzyloxy)-3-(benzyloxymethyl)-2,8-dioxabicyclo[3.3.1]non-6-ene

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Technology Process of (1S,3R,4S,5R)-4-(benzyloxy)-3-(benzyloxymethyl)-2,8-dioxabicyclo[3.3.1]non-6-ene

There total 7 articles about (1S,3R,4S,5R)-4-(benzyloxy)-3-(benzyloxymethyl)-2,8-dioxabicyclo[3.3.1]non-6-ene 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: 83.0%

: 1581705-01-2
2-[(2R,3S,4S)-3-(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyran-4-yl]acetaldehyde

: 1581705-02-3
(1S,3R,4S,5R)-4-(benzyloxy)-3-(benzyloxymethyl)-2,8-dioxabicyclo[3.3.1]non-6-ene

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -40 ℃; for 1h; stereoselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1002/ejoc.201301665

Reference yield:

: 2873-29-2
D-glucal triacetate

: 1581705-02-3
(1S,3R,4S,5R)-4-(benzyloxy)-3-(benzyloxymethyl)-2,8-dioxabicyclo[3.3.1]non-6-ene

Guidance literature:: Multi-step reaction with 7 steps

1.1: boron trifluoride diethyl etherate / benzene / 0 - 25 °C / Inert atmosphere

2.1: methanol; potassium carbonate / 3 h / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran / 1.33 h / 0 °C / Inert atmosphere

3.2: 25 °C / Inert atmosphere

4.1: sodium periodate; sodium hydrogencarbonate / methanol; water / 1 h / 25 °C / Inert atmosphere

5.1: diisopropylamine / benzene / 0.5 h / Inert atmosphere; Reflux

6.1: N,N-dimethyl-aniline / nitrobenzene / 150 - 170 °C / Inert atmosphere

7.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -40 °C / Inert atmosphere; Molecular sieve

With methanol; sodium periodate; trimethylsilyl trifluoromethanesulfonate; boron trifluoride diethyl etherate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; N,N-dimethyl-aniline; diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; nitrobenzene; benzene; 1.1: |Ferrier Carbohydrate Rearrangement / 6.1: |Claisen Rearrangement;
DOI:10.1002/ejoc.201301665

Reference yield:

: 1581704-97-3
2-phenylselenenylethyl 4,6-di-O-benzyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside

: 1581705-02-3
(1S,3R,4S,5R)-4-(benzyloxy)-3-(benzyloxymethyl)-2,8-dioxabicyclo[3.3.1]non-6-ene

Guidance literature:: Multi-step reaction with 4 steps

1: sodium periodate; sodium hydrogencarbonate / methanol; water / 1 h / 25 °C / Inert atmosphere

2: diisopropylamine / benzene / 0.5 h / Inert atmosphere; Reflux

3: N,N-dimethyl-aniline / nitrobenzene / 150 - 170 °C / Inert atmosphere

4: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / -40 °C / Inert atmosphere; Molecular sieve

With sodium periodate; trimethylsilyl trifluoromethanesulfonate; sodium hydrogencarbonate; N,N-dimethyl-aniline; diisopropylamine; In methanol; dichloromethane; water; nitrobenzene; benzene; 3: |Claisen Rearrangement;
DOI:10.1002/ejoc.201301665