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

Base Information

• Chemical Name: 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
• CAS No.: 111436-92-1
• Molecular Formula: C₅₀H₆₆O₁₁Si
• Molecular Weight: 871.153

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 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

There total 11 articles about 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 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:

Benzyloxymethyl chloride (3587-60-8) → 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 (111436-92-1)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH / dimethylformamide

2: LiAlH₄ / tetrahydrofuran

3: NBS / CHCl₃ / Heating

4: n-BuLi, sec-BuLi / tetrahydrofuran / -78 °C

5: 1.) LDA, 2.) CH₃SO₂Cl, Et₃N / 1.) THF, -78 degC

With N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; sec.-butyllithium; sodium hydride; methanesulfonyl chloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/ja00258a077

Reference yield:

1-carbomethoxy-3,5-dihydroxybenzene (2150-44-9) → 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 (111436-92-1)

Guidance literature:

Multi-step reaction with 5 steps

1: NaH / dimethylformamide

2: LiAlH₄ / tetrahydrofuran

3: NBS / CHCl₃ / Heating

4: n-BuLi, sec-BuLi / tetrahydrofuran / -78 °C

5: 1.) LDA, 2.) CH₃SO₂Cl, Et₃N / 1.) THF, -78 degC

With N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; sec.-butyllithium; sodium hydride; methanesulfonyl chloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/ja00258a077

Reference yield:

(E)-(4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-5-((2S,3R)-3-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-pent-2-enal (111436-89-6) → 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 (111436-92-1)

Guidance literature:

Multi-step reaction with 3 steps

1: TMSCl / diethyl ether; tetrahydrofuran / -78 °C

3: 1.) LDA, 2.) CH₃SO₂Cl, Et₃N / 1.) THF, -78 degC

With chloro-trimethyl-silane; methanesulfonyl chloride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ja00258a077

upstream raw materials:

methanesulfonyl chloride

Methyl 5(R),6(S),7(R),8(S),9(R)-6-methoxy-8,9-dihydroxy-7-<(tert-butyldimethylsilyl)oxy>-5-vinyldec-2(E)-enoate 8,9-cyclohexyl ketal

5,7-Bis-benzyloxymethoxy-3H-isobenzofuran-1-one

Benzyloxymethyl chloride

Downstream raw materials:

6,8,9-Tris-benzyloxymethoxy-3-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methoxy-2-((2S,3R)-3-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-ethyl]-1-oxo-1,2,3,4-tetrahydro-anthracene-2-carboxylic acid methyl ester

3-<1'-<<1'(S),2'(R),3'(S),4'(R)>-3',4'--1'-methoxy-2'-oxopentyl>>-6,8,9-tris<(benzyloxy)methoxy>-1,2,3,4-tetrahydro-2-<(tert-butyldimethylsilyl)oxy>-1(2H)-anthracenone

Methyl 3-<1'-<<2'(R),3'(S),4'(R),5'(S),6'(R)>-2'-<1-(2-hydroxyethyl)>-3'-methoxy-5',6'--4'-<(tert-butyldimethylsilyl)oxy>heptyl>>-1,6,8-tris<(benzyloxy)methoxy>-2-naphthoate

Methyl 3-<1'-<<2'(R),3'(S),4'(R),5'(S),6'(R)>-3'-methoxy-5',6'--2'-(2-oxoethyl)-4'-<(tert-butyldimethylsilyl)oxy>heptyl>>-1,6,8-tris<(benzyloxy)methoxy>-2-naphthoate

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