(1R,2R,3R,5S,6R,8R,9R,10S,12R)-5,6-Bis-benzyloxymethyl-2-bromo-8-methoxy-12-methyl-4,7-dioxa-tricyclo[7.2.1.0^3,10]dodecane

Base Information

• Chemical Name: (1R,2R,3R,5S,6R,8R,9R,10S,12R)-5,6-Bis-benzyloxymethyl-2-bromo-8-methoxy-12-methyl-4,7-dioxa-tricyclo[7.2.1.0^3,10]dodecane
• CAS No.: 199122-39-9
• Molecular Formula: C₂₈H₃₅BrO₅
• Molecular Weight: 531.487

Synonyms:(1R,2R,3R,5S,6R,8R,9R,10S,12R)-5,6-Bis-benzyloxymethyl-2-bromo-8-methoxy-12-methyl-4,7-dioxa-tricyclo[7.2.1.0^3,10]dodecane

Chemical Property of (1R,2R,3R,5S,6R,8R,9R,10S,12R)-5,6-Bis-benzyloxymethyl-2-bromo-8-methoxy-12-methyl-4,7-dioxa-tricyclo[7.2.1.0^3,10]dodecane

Chemical Property:

Purity/Quality:

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Technology Process of (1R,2R,3R,5S,6R,8R,9R,10S,12R)-5,6-Bis-benzyloxymethyl-2-bromo-8-methoxy-12-methyl-4,7-dioxa-tricyclo[7.2.1.0^3,10]dodecane

There total 5 articles about (1R,2R,3R,5S,6R,8R,9R,10S,12R)-5,6-Bis-benzyloxymethyl-2-bromo-8-methoxy-12-methyl-4,7-dioxa-tricyclo[7.2.1.0^3,10]dodecane 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: 90.0%

methanol (67-56-1) + (2S,4R,5S)-4,5-Bis-benzyloxymethyl-2-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-[1,3]dioxolane (199122-25-3) → (1R,2R,3R,5S,6R,8R,9R,10S,12R)-5,6-Bis-benzyloxymethyl-2-bromo-8-methoxy-12-methyl-4,7-dioxa-tricyclo[7.2.1.03,10]dodecane (199122-39-9)

Guidance literature:

With N-Bromosuccinimide; In acetonitrile; at -40 - 0 ℃;

DOI:10.1021/ja971881l

Reference yield:

(1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-en-2-carboxaldehyde (153380-53-1) → (1R,2R,3R,5S,6R,8R,9R,10S,12R)-5,6-Bis-benzyloxymethyl-2-bromo-8-methoxy-12-methyl-4,7-dioxa-tricyclo[7.2.1.03,10]dodecane (199122-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / pyridinium p-toluenesulfonate / toluene / 12 h / 20 °C

2: 86 percent / γ-collidine; N-bromosuccinimide / acetonitrile / -40 - 20 °C

With 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; pyridinium p-toluenesulfonate; In toluene; acetonitrile;

DOI:10.1016/S0040-4020(00)00859-0

Reference yield:

(2R*,3S*)-1,4-bis(benzyloxy)butane-2,3-diol (69010-01-1) → (1R,2R,3R,5S,6R,8R,9R,10S,12R)-5,6-Bis-benzyloxymethyl-2-bromo-8-methoxy-12-methyl-4,7-dioxa-tricyclo[7.2.1.03,10]dodecane (199122-39-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / pyridinium p-toluenesulfonate / toluene / 12 h / 20 °C

2: 86 percent / γ-collidine; N-bromosuccinimide / acetonitrile / -40 - 20 °C

With 2,4,6-trimethyl-pyridine; N-Bromosuccinimide; pyridinium p-toluenesulfonate; In toluene; acetonitrile;

DOI:10.1016/S0040-4020(00)00859-0

upstream raw materials:

methanol

(2S,4R,5S)-4,5-Bis-benzyloxymethyl-2-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-[1,3]dioxolane

(1R,2R,3S,4S)-3-methylbicyclo[2.2.1]hept-5-en-2-carboxaldehyde

(2R*,3S*)-1,4-bis(benzyloxy)butane-2,3-diol

Downstream raw materials:

(2S,3R)-1,4-Bis-benzyloxy-3-[(R)-methoxy-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-methoxy]-butan-2-ol

(1S,4R,5R,6S)-5-[(R)-((1R,2S)-2-Benzyloxy-1-isopropyl-3-methyl-butoxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

(2S,4R,5S)-4,5-Bis-benzyloxymethyl-2-((1R,2R,3S,4S)-3-methyl-bicyclo[2.2.1]hept-5-en-2-yl)-[1,3]dioxolane

(1S,4R,5R,6S)-5-[(R)-((1R,2S)-2,3-Bis-benzyloxy-1-benzyloxymethyl-propoxy)-methoxy-methyl]-6-methyl-bicyclo[2.2.1]hept-2-ene

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