(2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(tert-butyldimethylsiloxy)-8-chloro-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxononanal

Base Information

• Chemical Name: (2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(tert-butyldimethylsiloxy)-8-chloro-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxononanal
• CAS No.: 253663-00-2
• Molecular Formula: C₃₉H₅₃ClO₇Si
• Molecular Weight: 697.384

Synonyms:(2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(tert-butyldimethylsiloxy)-8-chloro-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxononanal

Chemical Property of (2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(tert-butyldimethylsiloxy)-8-chloro-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxononanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(tert-butyldimethylsiloxy)-8-chloro-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxononanal

There total 20 articles about (2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(tert-butyldimethylsiloxy)-8-chloro-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxononanal 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: 92.0%

(4R,5R,7R,8S)-4,8-bis(benzyloxy)-5-(t-butyldimethylsiloxy)-2-chloro-9-hydroxy-7-(4-methoxybenzyloxy)-6,6-dimethylnonan-3-one (333956-98-2) → (2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(tert-butyldimethylsiloxy)-8-chloro-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxononanal (253663-00-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1246/cl.1999.1145

Reference yield:

(2R)-(-)-3,3-dimethylbutane-1,2,4-triol (60856-63-5) → (2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(tert-butyldimethylsiloxy)-8-chloro-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxononanal (253663-00-2)

Guidance literature:

Multi-step reaction with 14 steps

1.1: camphorsulfonic acid / CH₂Cl₂ / 2 h / 20 °C

1.2: 92 percent / Et₃N / CH₂Cl₂

2.1: 21.2 g / oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

3.1: 86 percent / n-BuLi / hexane; tetrahydrofuran / -15 - 20 °C

4.1: OsO₄; N-methylmorpholine-N-oxide / H₂O; acetone; 2-methyl-propan-2-ol / 72 h / 2 °C

5.1: 100 percent / imidazole / dimethylformamide / 1 h / 0 °C

6.1: 96 percent / NaH / tetrahydrofuran; dimethylformamide / 18 h / 0 - 20 °C

7.1: 85 percent / BH₃*Me₂S / toluene / 0.5 h / Heating

8.1: 67 percent / oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

9.1: 87 percent / MgBr₂*Et₂O / toluene / 1 h / -19 °C

10.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

11.1: 78 percent / n-BuLi / hexane; diethyl ether; tetrahydrofuran / 1 h / -100 - -78 °C

12.1: 90 percent / Bu₃SnH / benzene / 0.5 h / Heating

13.1: 93 percent / aq. HCl / tetrahydrofuran / 12 h / 0 - 20 °C

14.1: 92 percent / oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; osmium(VIII) oxide; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; camphor-10-sulfonic acid; tri-n-butyl-tin hydride; sodium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; magnesium bromide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; benzene; 2.1: Swern's oxidation / 3.1: Wittig reaction / 8.1: Swern's oxidation / 14.1: Swern's oxidation;

DOI:10.1246/bcsj.74.113

Reference yield:

(Z)-2-benzyloxy-1-methoxy-1-(trimethylsiloxy)ethene (139400-25-2) → (2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(tert-butyldimethylsiloxy)-8-chloro-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxononanal (253663-00-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / MgBr₂*Et₂O / toluene / 1 h / -19 °C

2: 100 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

3: 78 percent / n-BuLi / hexane; diethyl ether; tetrahydrofuran / 1 h / -100 - -78 °C

4: 90 percent / Bu₃SnH / benzene / 0.5 h / Heating

5: 93 percent / aq. HCl / tetrahydrofuran / 12 h / 0 - 20 °C

6: 92 percent / oxalyl chloride; DMSO / CH₂Cl₂ / -78 - 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; n-butyllithium; oxalyl dichloride; tri-n-butyl-tin hydride; dimethyl sulfoxide; magnesium bromide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; benzene; 6: Swern's oxidation;

DOI:10.1246/bcsj.74.113

upstream raw materials:

(4R,5R,7R,8S)-4,8-bis(benzyloxy)-5-(t-butyldimethylsiloxy)-2-chloro-9-hydroxy-7-(4-methoxybenzyloxy)-6,6-dimethylnonan-3-one

methyl 2-(benzyloxy)acetate

t-butyldimethylsiyl triflate

benzyl bromide

Downstream raw materials:

(2R,3R,5R,6S,7S*,8R)-2,6-Dibenzyloxy-3-(tert-butyldimethylsiloxy)-7-hydroxy-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

(2R,3R,5R,6S,7R,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsiloxy)-7-hydroxy-5-(4-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

(2R,3R,5R,6S,7S,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsiloxy)-7-hydroxy-5-(4-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

(2R,3R,5R,6R,7R,8R)-7-Acetoxy-2,6-dibenzyloxy-3-(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4,8-trimethylcyclooctanone

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