(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-7-[1,3]dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-heptanoic acid benzyl ester

Base Information

Chemical Name:(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-7-[1,3]dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-heptanoic acid benzyl ester
CAS No.:161926-49-4
Molecular Formula:C₃₇H₅₆O₈Si
Molecular Weight:656.932
Hs Code.:

Synonyms:(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-7-[1,3]dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-heptanoic acid benzyl ester

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Chemical Property of (3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-7-[1,3]dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-heptanoic acid benzyl ester

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Technology Process of (3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-7-[1,3]dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-heptanoic acid benzyl ester

There total 10 articles about (3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-7-[1,3]dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-heptanoic acid benzyl ester 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: 83.0%

: 107-21-1
ethylene glycol

: 161926-48-3
(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-3,5-dimethyl-8-oxo-6-triisopropylsilanyloxy-octanoic acid benzyl ester

: 161926-49-4
(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-7-[1,3]dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-heptanoic acid benzyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; for 0.25h; -78 degC -> 0 degC;
DOI:10.1016/0040-4039(94)02427-D

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 161926-49-4
(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-7-[1,3]dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-heptanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent

2: 1.) O₃, pyridine, 2.) Me₂S / 1.) MeOH, CH₂Cl₂, -78 deg C, 2.) MeOH, CH₂Cl₂, RT, 12 h

3: BF₃*EtO₂

With pyridine; dimethylsulfide; boron trifluoride diethyl etherate; ozone;
DOI:10.1021/ja9743194

Reference yield:

: 161926-42-7
1,1-bis(benzyloxy)propan-2-one

: 161926-49-4
(3R,4R,5R,6S)-3-Acetoxy-4-benzyloxy-7-[1,3]dioxolan-2-yl-3,5-dimethyl-6-triisopropylsilanyloxy-heptanoic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 56 percent / TMSOTf / CH₂Cl₂ / 13 h / -78 degC -> -35 degC

2: 1.) LiN(TMS)2; 2.) NEt₃ / 2.) DMAP / 1.) THF, -78 degC; 2.) CH₂Cl₂, 0 degC -> r.t.

3: 83 percent / O₃, methyl sulfide / methanol / 15 h / -78 degC -> r.t.

4: TiCl₄ / CH₂Cl₂ / 8 h / -78 °C

5: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0 °C

6: 90 percent / O₃, methyl sulfide / methanol / 15 h / -78 degC -> r.t.

7: 83 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.25 h / -78 degC -> 0 degC

With 2,6-dimethylpyridine; dimethylsulfide; boron trifluoride diethyl etherate; titanium tetrachloride; ozone; triethylamine; lithium hexamethyldisilazane; dmap; trimethylsilyl trifluoromethanesulfonate; In methanol; dichloromethane;
DOI:10.1016/0040-4039(94)02427-D