(1S,3R,7R,8S,12S)-8-(benzyloxy)-1-[(benzyloxy)methyl]-5,5-dimethyl-12-hydroxy-2,4,6-trioxatricyclo[6.4.0.0^3,7]dodec-10-ene

Base Information

• Chemical Name: (1S,3R,7R,8S,12S)-8-(benzyloxy)-1-[(benzyloxy)methyl]-5,5-dimethyl-12-hydroxy-2,4,6-trioxatricyclo[6.4.0.0^3,7]dodec-10-ene
• CAS No.: 696599-35-6
• Molecular Formula: C₂₆H₃₀O₆
• Molecular Weight: 438.521

Synonyms:(1S,3R,7R,8S,12S)-8-(benzyloxy)-1-[(benzyloxy)methyl]-5,5-dimethyl-12-hydroxy-2,4,6-trioxatricyclo[6.4.0.0^3,7]dodec-10-ene

Chemical Property of (1S,3R,7R,8S,12S)-8-(benzyloxy)-1-[(benzyloxy)methyl]-5,5-dimethyl-12-hydroxy-2,4,6-trioxatricyclo[6.4.0.0^3,7]dodec-10-ene

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Technology Process of (1S,3R,7R,8S,12S)-8-(benzyloxy)-1-[(benzyloxy)methyl]-5,5-dimethyl-12-hydroxy-2,4,6-trioxatricyclo[6.4.0.0^3,7]dodec-10-ene

There total 6 articles about (1S,3R,7R,8S,12S)-8-(benzyloxy)-1-[(benzyloxy)methyl]-5,5-dimethyl-12-hydroxy-2,4,6-trioxatricyclo[6.4.0.0^3,7]dodec-10-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: 93.0%

3-C-allyl-3,5-di-O-benzyl-4-C-(1(S)-hydroxyallyl)-1,2-di-O-isopropylidene-α-D-ribofuranose (485755-38-2) → (1S,3R,7R,8S,12S)-8-(benzyloxy)-1-[(benzyloxy)methyl]-5,5-dimethyl-12-hydroxy-2,4,6-trioxatricyclo[6.4.0.03,7]dodec-10-ene (696599-35-6)

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; for 24h; Heating;

DOI:10.1016/j.tet.2004.03.019

Reference yield:

benzyl bromide (100-39-0) → (1S,3R,7R,8S,12S)-8-(benzyloxy)-1-[(benzyloxy)methyl]-5,5-dimethyl-12-hydroxy-2,4,6-trioxatricyclo[6.4.0.03,7]dodec-10-ene (696599-35-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 61 percent / NaH / dimethylformamide / 1 h / 20 °C

2: PCC / CH₂Cl₂ / 42 h / 20 °C

3: 2.95 g / tetrahydrofuran / 17 h / 20 °C

4: 93 percent / Grubbs' catalyst / CH₂Cl₂ / 24 h / Heating

With Grubbs catalyst first generation; sodium hydride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.03.019

Reference yield:

(3aR,5R,6S,6aR)-6-Allyl-6-benzyloxy-5-benzyloxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carbaldehyde → (1S,3R,7R,8S,12S)-8-(benzyloxy)-1-[(benzyloxy)methyl]-5,5-dimethyl-12-hydroxy-2,4,6-trioxatricyclo[6.4.0.03,7]dodec-10-ene (696599-35-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.95 g / tetrahydrofuran / 17 h / 20 °C

2: 93 percent / Grubbs' catalyst / CH₂Cl₂ / 24 h / Heating

With Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2004.03.019

upstream raw materials:

3-C-allyl-3,5-di-O-benzyl-4-C-(1(S)-hydroxyallyl)-1,2-di-O-isopropylidene-α-D-ribofuranose

benzyl bromide

3-C-allyl-3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

3-C-allyl-3,5-di-O-benzyl-4-C-hydroxymethyl-1,2-di-O-isopropylidene-α-D-ribofuranose

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