(3aR,5S,6S,6aR)-6-Benzyloxy-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

Base Information

Chemical Name:(3aR,5S,6S,6aR)-6-Benzyloxy-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde
CAS No.:473290-47-0
Molecular Formula:C₂₃H₂₆O₆
Molecular Weight:398.456
Hs Code.:

Synonyms:(3aR,5S,6S,6aR)-6-Benzyloxy-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

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Chemical Property of (3aR,5S,6S,6aR)-6-Benzyloxy-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

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Technology Process of (3aR,5S,6S,6aR)-6-Benzyloxy-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

There total 7 articles about (3aR,5S,6S,6aR)-6-Benzyloxy-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde 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:

: 153186-11-9
{(1S,3S,4S,5R)-7,7-dimethyl-2,6,8-trioxa-4-(phenylmethoxy)-3-[(phenylmethoxy)methyl]-bicyclo[3.3.0]oct-3-yl}methan-1-ol

: 473290-47-0
(3aR,5S,6S,6aR)-6-Benzyloxy-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

Guidance literature:: With dichloro-acetic acid; dicyclohexyl-carbodiimide; In dimethyl sulfoxide; at 20 ℃;
DOI:10.1016/S0040-4020(02)00477-5

Reference yield:

: 63593-02-2
3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdo-1,4-furanose

: 473290-47-0
(3aR,5S,6S,6aR)-6-Benzyloxy-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1: 94 percent / aq. NaOH / dioxane

2: 38 percent / n-BuLi / hexane; tetrahydrofuran / 1 h / Heating

3: 76 percent / NaH; n-Bu₄NI / tetrahydrofuran / 3 h / 20 °C

4: 93 percent / n-Bu₄NF / tetrahydrofuran / 20 °C

5: dicyclohexylcarbodiimide; dichloroacetic acid / dimethylsulfoxide / 20 °C

With dichloro-acetic acid; sodium hydroxide; n-butyllithium; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; hexane; dimethyl sulfoxide; 1: Cannizzaro reaction;
DOI:10.1016/S0040-4020(02)00477-5

Reference yield:

: 57099-04-4
3-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose

: 473290-47-0
(3aR,5S,6S,6aR)-6-Benzyloxy-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: aq. NaIO₄ / methanol

2: 94 percent / aq. NaOH / dioxane

3: 38 percent / n-BuLi / hexane; tetrahydrofuran / 1 h / Heating

4: 76 percent / NaH; n-Bu₄NI / tetrahydrofuran / 3 h / 20 °C

5: 93 percent / n-Bu₄NF / tetrahydrofuran / 20 °C

6: dicyclohexylcarbodiimide; dichloroacetic acid / dimethylsulfoxide / 20 °C

With dichloro-acetic acid; sodium hydroxide; sodium periodate; n-butyllithium; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dimethyl sulfoxide; 2: Cannizzaro reaction;
DOI:10.1016/S0040-4020(02)00477-5