(2R,4aR,6S,7R,9R,9aS)-7,9-Bis-benzyloxy-6-(2-benzyloxy-ethyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene

Base Information

• Chemical Name: (2R,4aR,6S,7R,9R,9aS)-7,9-Bis-benzyloxy-6-(2-benzyloxy-ethyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene
• CAS No.: 342901-73-9
• Molecular Formula: C₃₇H₄₀O₆
• Molecular Weight: 580.721

Synonyms:(2R,4aR,6S,7R,9R,9aS)-7,9-Bis-benzyloxy-6-(2-benzyloxy-ethyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene

Chemical Property of (2R,4aR,6S,7R,9R,9aS)-7,9-Bis-benzyloxy-6-(2-benzyloxy-ethyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,6S,7R,9R,9aS)-7,9-Bis-benzyloxy-6-(2-benzyloxy-ethyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene

There total 8 articles about (2R,4aR,6S,7R,9R,9aS)-7,9-Bis-benzyloxy-6-(2-benzyloxy-ethyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene 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: 84.0%

benzyl bromide (100-39-0) + (2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-6-(2-hydroxy-ethyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol (342901-72-8) → (2R,4aR,6S,7R,9R,9aS)-7,9-Bis-benzyloxy-6-(2-benzyloxy-ethyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene (342901-73-9)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1002/1521-3773(20010316)40:6<1090::AID-ANIE10900>3.0.CO;2-W

Reference yield:

benzyl bromide (100-39-0) → (2R,4aR,6S,7R,9R,9aS)-7,9-Bis-benzyloxy-6-(2-benzyloxy-ethyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene (342901-73-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-Bu₂SnO / benzene / Heating

1.2: CsF / dimethylformamide / 20 °C

2.1: NaH; CS₂; MeI / tetrahydrofuran / 20 °C

2.2: n-Bu₃SnH; AIBN / benzene / Heating

3.1: conc. HCl / CHCl₃ / 20 °C

3.2: 46 percent / camphorsulfonic acid / CH₂Cl₂ / 20 °C

4.1: 97 percent / N-methylmorpholine / CH₂Cl₂ / 20 °C

5.1: 98 percent / MeI; NaHCO₃ / acetonitrile; H₂O / 20 °C

6.1: SmI₂; HMPA / methanol; tetrahydrofuran / 0 °C

7.1: LiAlH₄ / tetrahydrofuran / 20 °C

8.1: 84 percent / NaH / dimethylformamide / 20 °C

With 4-methyl-morpholine; hydrogenchloride; carbon disulfide; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; samarium diiodide; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1002/1521-3773(20010316)40:6<1090::AID-ANIE10900>3.0.CO;2-W

Reference yield:

(2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (2774-19-8,14419-69-3,15887-67-9,23392-28-1,57539-08-9,61277-63-2,74410-51-8,76419-48-2,80734-73-2,86363-44-2,89301-79-1,94061-92-4,94062-87-0,108739-92-0,129706-93-0,143005-12-3,65877-21-6) → (2R,4aR,6S,7R,9R,9aS)-7,9-Bis-benzyloxy-6-(2-benzyloxy-ethyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocycloheptene (342901-73-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: NaH; CS₂; MeI / tetrahydrofuran / 20 °C

1.2: n-Bu₃SnH; AIBN / benzene / Heating

2.1: conc. HCl / CHCl₃ / 20 °C

2.2: 46 percent / camphorsulfonic acid / CH₂Cl₂ / 20 °C

3.1: 97 percent / N-methylmorpholine / CH₂Cl₂ / 20 °C

4.1: 98 percent / MeI; NaHCO₃ / acetonitrile; H₂O / 20 °C

5.1: SmI₂; HMPA / methanol; tetrahydrofuran / 0 °C

6.1: LiAlH₄ / tetrahydrofuran / 20 °C

7.1: 84 percent / NaH / dimethylformamide / 20 °C

With 4-methyl-morpholine; hydrogenchloride; carbon disulfide; N,N,N,N,N,N-hexamethylphosphoric triamide; lithium aluminium tetrahydride; samarium diiodide; sodium hydride; sodium hydrogencarbonate; methyl iodide; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/1521-3773(20010316)40:6<1090::AID-ANIE10900>3.0.CO;2-W

upstream raw materials:

benzyl bromide

(2R,4aR,6S,7R,9R,9aS)-9-Benzyloxy-6-(2-hydroxy-ethyl)-2-phenyl-hexahydro-1,3,5-trioxa-benzocyclohepten-7-ol

(2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-arabino-hexopyranoside

Downstream raw materials:

(2R,3S,4R,6R,7S)-4,6-Bis-benzyloxy-7-(2-benzyloxy-ethyl)-2-hydroxymethyl-oxepan-3-ol

C₇₅H₁₀₂O₁₃Si

C₇₅H₁₀₀O₁₂Si

C₇₁H₉₀O₁₂S

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