(E)-(2R,5R,6S)-6-Benzyloxy-3,13,20-trioxa-tricyclo[13.2.2.1^2,5]icosa-1⁽¹⁸⁾,8,15⁽¹⁹⁾,16-tetraen-14-one

Base Information

• Chemical Name: (E)-(2R,5R,6S)-6-Benzyloxy-3,13,20-trioxa-tricyclo[13.2.2.1^2,5]icosa-1⁽¹⁸⁾,8,15⁽¹⁹⁾,16-tetraen-14-one
• CAS No.: 211692-00-1
• Molecular Formula: C₂₄H₂₆O₅
• Molecular Weight: 394.467
• Mol file: 211692-00-1.mol

Synonyms:(E)-(2R,5R,6S)-6-Benzyloxy-3,13,20-trioxa-tricyclo[13.2.2.1^2,5]icosa-1⁽¹⁸⁾,8,15⁽¹⁹⁾,16-tetraen-14-one

Chemical Property of (E)-(2R,5R,6S)-6-Benzyloxy-3,13,20-trioxa-tricyclo[13.2.2.1^2,5]icosa-1⁽¹⁸⁾,8,15⁽¹⁹⁾,16-tetraen-14-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2R,5R,6S)-6-Benzyloxy-3,13,20-trioxa-tricyclo[13.2.2.1^2,5]icosa-1⁽¹⁸⁾,8,15⁽¹⁹⁾,16-tetraen-14-one

There total 11 articles about (E)-(2R,5R,6S)-6-Benzyloxy-3,13,20-trioxa-tricyclo[13.2.2.1^2,5]icosa-1⁽¹⁸⁾,8,15⁽¹⁹⁾,16-tetraen-14-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:

(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol (79364-35-5) → (E)-(2R,5R,6S)-6-Benzyloxy-3,13,20-trioxa-tricyclo[13.2.2.12,5]icosa-1(18),8,15(19),16-tetraen-14-one (211692-00-1)

Guidance literature:

Multi-step reaction with 10 steps

1: NaH, imidazole / dimethylformamide

2: 1.) O₃, 2.) PPH₃ / 1.) CH₂Cl₂, 2.) CH₂Cl₂

3: tetrahydrofuran / 0 °C

4: 79 percent / EtCO₂H / toluene / Heating

5: LiAlH₄ / tetrahydrofuran / 0 °C

6: Et₃N / CH₂Cl₂

7: AcOH, H₂O

8: TsOH, molecular sieves 4 Angstroem

9: H₂O, LiOH / methanol; tetrahydrofuran

10: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 2 h, 2.) THF, toluene, reflux, 20 h

With 1H-imidazole; dmap; lithium hydroxide; lithium aluminium tetrahydride; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; water; sodium hydride; toluene-4-sulfonic acid; ozone; acetic acid; propionic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/(SICI)1521-3773(19980619)37:11<1566::AID-ANIE1566>3.0.CO;2-U

Reference yield:

(R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane (87604-53-3) → (E)-(2R,5R,6S)-6-Benzyloxy-3,13,20-trioxa-tricyclo[13.2.2.12,5]icosa-1(18),8,15(19),16-tetraen-14-one (211692-00-1)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) O₃, 2.) PPH₃ / 1.) CH₂Cl₂, 2.) CH₂Cl₂

2: tetrahydrofuran / 0 °C

3: 79 percent / EtCO₂H / toluene / Heating

4: LiAlH₄ / tetrahydrofuran / 0 °C

5: Et₃N / CH₂Cl₂

6: AcOH, H₂O

7: TsOH, molecular sieves 4 Angstroem

8: H₂O, LiOH / methanol; tetrahydrofuran

9: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 2 h, 2.) THF, toluene, reflux, 20 h

With dmap; lithium hydroxide; lithium aluminium tetrahydride; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; water; toluene-4-sulfonic acid; ozone; acetic acid; propionic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1002/(SICI)1521-3773(19980619)37:11<1566::AID-ANIE1566>3.0.CO;2-U

Reference yield:

(3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal (103795-36-4) → (E)-(2R,5R,6S)-6-Benzyloxy-3,13,20-trioxa-tricyclo[13.2.2.12,5]icosa-1(18),8,15(19),16-tetraen-14-one (211692-00-1)

Guidance literature:

Multi-step reaction with 8 steps

1: tetrahydrofuran / 0 °C

2: 79 percent / EtCO₂H / toluene / Heating

3: LiAlH₄ / tetrahydrofuran / 0 °C

4: Et₃N / CH₂Cl₂

5: AcOH, H₂O

6: TsOH, molecular sieves 4 Angstroem

7: H₂O, LiOH / methanol; tetrahydrofuran

8: 1.) 2,4,6-trichlorobenzoyl chloride, Et₃N, 2.) DMAP / 1.) THF, 2 h, 2.) THF, toluene, reflux, 20 h

With dmap; lithium hydroxide; lithium aluminium tetrahydride; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; water; toluene-4-sulfonic acid; acetic acid; propionic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1002/(SICI)1521-3773(19980619)37:11<1566::AID-ANIE1566>3.0.CO;2-U

upstream raw materials:

4-[(2R,4R)-4-((E)-(S)-1-Benzyloxy-7-hydroxy-hept-3-enyl)-[1,3]dioxolan-2-yl]-benzoic acid

(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

(3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal

(R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane

Downstream raw materials:

C₂₄H₂₆O₆

(2R,5R,6S,8R,9R)-6-Benzyloxy-8,9-dihydroxy-3,13,20-trioxa-tricyclo[13.2.2.1^2,5]icosa-1⁽¹⁸⁾,15⁽¹⁹⁾,16-trien-14-one