methyl 4-<(benzyloxy)methoxy>-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate

Base Information

• Chemical Name: methyl 4-<(benzyloxy)methoxy>-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate
• CAS No.: 144107-96-0
• Molecular Formula: C₃₈H₅₄O₁₀Si
• Molecular Weight: 698.926

Synonyms:methyl 4-<(benzyloxy)methoxy>-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate

Chemical Property of methyl 4-<(benzyloxy)methoxy>-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate

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Technology Process of methyl 4-<(benzyloxy)methoxy>-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate

There total 4 articles about methyl 4-<(benzyloxy)methoxy>-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate 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: 80.0%

(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-3-((2S,3R)-3-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-propionaldehyde (111436-88-5) + dimethyl <3-<5'-<(benzyloxy)methoxy>-2'-(methoxycarbonyl)-3'-hydroxyphenyl>-2-oxopropyl>phosphonate (144107-95-9) → methyl 4-<(benzyloxy)methoxy>-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate (144107-96-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In acetonitrile; at -5 ℃; for 2h;

DOI:10.1021/jo00050a047

Reference yield:

Benzyloxymethyl chloride (3587-60-8) → methyl 4-<(benzyloxy)methoxy>-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate (144107-96-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / K₂CO₃*1.5 H₂O / acetone / 2 h / 30 °C

2: 57 percent / tetrahydrofuran; hexane / 3 h / -78 °C

3: 80 percent / LiCl, DBU / acetonitrile / 2 h / -5 °C

With potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; hexane; acetone; acetonitrile;

DOI:10.1021/jo00050a047

Reference yield:

methyl <3,5-dihydroxy-2-(methoxycarbonyl)phenyl>acetate (6110-30-1) → methyl 4-<(benzyloxy)methoxy>-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate (144107-96-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / K₂CO₃*1.5 H₂O / acetone / 2 h / 30 °C

2: 57 percent / tetrahydrofuran; hexane / 3 h / -78 °C

3: 80 percent / LiCl, DBU / acetonitrile / 2 h / -5 °C

With potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; hexane; acetone; acetonitrile;

DOI:10.1021/jo00050a047

upstream raw materials:

(2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methoxy-3-((2S,3R)-3-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-propionaldehyde

dimethyl <3-<5'-<(benzyloxy)methoxy>-2'-(methoxycarbonyl)-3'-hydroxyphenyl>-2-oxopropyl>phosphonate

Benzyloxymethyl chloride

methyl <3,5-dihydroxy-2-(methoxycarbonyl)phenyl>acetate

Downstream raw materials:

methyl 6,8-bis<(benzyloxy)methoxy>-1-hydroxy-3-<(2'R,3'S,4'R,5'S,6'R)-3'-methoxy-5',6'-(cyclohexylidenedioxy)-4'-<(tert-butyldimethylsilyl)oxy>-2'-vinylheptyl>naphthoate

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