(Z)-3-(4-Benzyloxy-phenyl)-1-((2R,3R,4S,4aR,9bS)-3,4-bis-benzyloxy-2-benzyloxymethyl-7-hydroxy-9-methoxy-3,4,4a,9b-tetrahydro-2H-benzo[4,5]furo[3,2-b]pyran-8-yl)-3-hydroxy-propenone

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Chemical Name:(Z)-3-(4-Benzyloxy-phenyl)-1-((2R,3R,4S,4aR,9bS)-3,4-bis-benzyloxy-2-benzyloxymethyl-7-hydroxy-9-methoxy-3,4,4a,9b-tetrahydro-2H-benzo[4,5]furo[3,2-b]pyran-8-yl)-3-hydroxy-propenone
CAS No.:720684-63-9
Molecular Formula:C₅₀H₄₆O₁₀
Molecular Weight:806.909
Hs Code.:

(Z)-3-(4-Benzyloxy-phenyl)-1-((2R,3R,4S,4aR,9bS)-3,4-bis-benzyloxy-2-benzyloxymethyl-7-hydroxy-9-methoxy-3,4,4a,9b-tetrahydro-2H-benzo[4,5]furo[3,2-b]pyran-8-yl)-3-hydroxy-propenone

Synonyms:(Z)-3-(4-Benzyloxy-phenyl)-1-((2R,3R,4S,4aR,9bS)-3,4-bis-benzyloxy-2-benzyloxymethyl-7-hydroxy-9-methoxy-3,4,4a,9b-tetrahydro-2H-benzo[4,5]furo[3,2-b]pyran-8-yl)-3-hydroxy-propenone

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Chemical Property of (Z)-3-(4-Benzyloxy-phenyl)-1-((2R,3R,4S,4aR,9bS)-3,4-bis-benzyloxy-2-benzyloxymethyl-7-hydroxy-9-methoxy-3,4,4a,9b-tetrahydro-2H-benzo[4,5]furo[3,2-b]pyran-8-yl)-3-hydroxy-propenone

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Technology Process of (Z)-3-(4-Benzyloxy-phenyl)-1-((2R,3R,4S,4aR,9bS)-3,4-bis-benzyloxy-2-benzyloxymethyl-7-hydroxy-9-methoxy-3,4,4a,9b-tetrahydro-2H-benzo[4,5]furo[3,2-b]pyran-8-yl)-3-hydroxy-propenone

There total 12 articles about (Z)-3-(4-Benzyloxy-phenyl)-1-((2R,3R,4S,4aR,9bS)-3,4-bis-benzyloxy-2-benzyloxymethyl-7-hydroxy-9-methoxy-3,4,4a,9b-tetrahydro-2H-benzo[4,5]furo[3,2-b]pyran-8-yl)-3-hydroxy-propenone 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: 50.0%

: 780788-96-7
4-Benzyloxy-benzoic acid (2R,3R,4S,4aR,9bS)-8-acetyl-3,4-bis-benzyloxy-2-benzyloxymethyl-9-methoxy-3,4,4a,9b-tetrahydro-2H-benzo[4,5]furo[3,2-b]pyran-7-yl ester

: 720684-63-9
(Z)-3-(4-Benzyloxy-phenyl)-1-((2R,3R,4S,4aR,9bS)-3,4-bis-benzyloxy-2-benzyloxymethyl-7-hydroxy-9-methoxy-3,4,4a,9b-tetrahydro-2H-benzo[4,5]furo[3,2-b]pyran-8-yl)-3-hydroxy-propenone

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -30 ℃;
DOI:10.1016/j.bmcl.2004.03.108

Reference yield:

: 55628-54-1
3,4,6-tri-O-benzyl-D-glucal

: 720684-63-9
(Z)-3-(4-Benzyloxy-phenyl)-1-((2R,3R,4S,4aR,9bS)-3,4-bis-benzyloxy-2-benzyloxymethyl-7-hydroxy-9-methoxy-3,4,4a,9b-tetrahydro-2H-benzo[4,5]furo[3,2-b]pyran-8-yl)-3-hydroxy-propenone

Guidance literature:: Multi-step reaction with 12 steps

1: 100 percent / dimethyloxirane / CH₂Cl₂ / 0 °C

2: 100 percent / CH₂Cl₂ / 20 °C

3: 63 percent / 2,4,6-collidine; AgOTf / 35 °C

4: 50 percent / aq. H₂SO₄; AcOH / Heating

5: 78 percent / (diethylamino)sulfur trifluoride / CH₂Cl₂ / -78 °C

6: 56 percent / BF₃*OEt₂; 4A molecular sieves / CH₂Cl₂ / -20 - 20 °C

7: 86 percent / NaH / dimethylformamide / 20 °C

8: 73 percent / indium; aq. NH₄Cl / methanol; propan-2-ol / 85 °C

9: 92 percent / H₂ / Pd/C / tetrahydrofuran / 20 °C

10: 73 percent / 1,1'-azobis(N,N-dimethylformamide); Bu₃P / benzene / 20 °C

11: 88 percent / DMAP / CH₂Cl₂ / 20 °C

12: 50 percent / LDA / tetrahydrofuran / -30 °C

With 2-methyl-1,2-epoxypropane; 2,4,6-trimethyl-pyridine; dmap; indium; tributylphosphine; diethylamino-sulfur trifluoride; diamide; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; hydrogen; silver trifluoromethanesulfonate; sodium hydride; ammonium chloride; acetic acid; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; benzene; 10: Mitsunobu reaction;
DOI:10.1016/j.bmcl.2004.03.108

Reference yield:

: 18065-05-9
1-[2,4-bis(benzyloxy)-6-hydroxyphenyl]ethanone

: 720684-63-9
(Z)-3-(4-Benzyloxy-phenyl)-1-((2R,3R,4S,4aR,9bS)-3,4-bis-benzyloxy-2-benzyloxymethyl-7-hydroxy-9-methoxy-3,4,4a,9b-tetrahydro-2H-benzo[4,5]furo[3,2-b]pyran-8-yl)-3-hydroxy-propenone

Guidance literature:: Multi-step reaction with 7 steps

1: 56 percent / BF₃*OEt₂; 4A molecular sieves / CH₂Cl₂ / -20 - 20 °C

2: 86 percent / NaH / dimethylformamide / 20 °C

3: 73 percent / indium; aq. NH₄Cl / methanol; propan-2-ol / 85 °C

4: 92 percent / H₂ / Pd/C / tetrahydrofuran / 20 °C

5: 73 percent / 1,1'-azobis(N,N-dimethylformamide); Bu₃P / benzene / 20 °C

6: 88 percent / DMAP / CH₂Cl₂ / 20 °C

7: 50 percent / LDA / tetrahydrofuran / -30 °C

With dmap; indium; tributylphosphine; diamide; 4 A molecular sieve; boron trifluoride diethyl etherate; hydrogen; sodium hydride; ammonium chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; benzene; 5: Mitsunobu reaction;
DOI:10.1016/j.bmcl.2004.03.108