(3S,4R,5R)-3,4-Bis-benzyloxy-5-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-pyrrolidin-2-one

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Chemical Name:(3S,4R,5R)-3,4-Bis-benzyloxy-5-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-pyrrolidin-2-one
CAS No.:220831-08-3
Molecular Formula:C₄₀H₅₃NO₆
Molecular Weight:643.864
Hs Code.:

Synonyms:(3S,4R,5R)-3,4-Bis-benzyloxy-5-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-pyrrolidin-2-one

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Chemical Property of (3S,4R,5R)-3,4-Bis-benzyloxy-5-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-pyrrolidin-2-one

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Technology Process of (3S,4R,5R)-3,4-Bis-benzyloxy-5-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-pyrrolidin-2-one

There total 9 articles about (3S,4R,5R)-3,4-Bis-benzyloxy-5-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-pyrrolidin-2-one 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: 96.0%

: 107-21-1
ethylene glycol

: 220831-11-8
(3S,4R,5R)-3,4-Bis-benzyloxy-5-(13-benzyloxy-10-oxo-tridecyl)-pyrrolidin-2-one

: 220831-08-3
(3S,4R,5R)-3,4-Bis-benzyloxy-5-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-pyrrolidin-2-one

Guidance literature:: With toluene-4-sulfonic acid; In benzene; Heating;
DOI:10.1016/S0040-4039(98)02605-7

Reference yield:

: 183312-54-1
3-benzyloxypropylmagnesium bromide

: 220831-08-3
(3S,4R,5R)-3,4-Bis-benzyloxy-5-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: tetrahydrofuran / 0 °C

2: 90 percent / PCC, MS 4A / CH₂Cl₂

3: 92 percent / Bu₄NF / tetrahydrofuran

4: 100 percent / Ag₂O / ethyl acetate

5: 70 percent / CAN / acetonitrile

6: 96 percent / p-TsOH / benzene / Heating

With ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; pyridinium chlorochromate; silver(l) oxide; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile; benzene;
DOI:10.1016/S0040-4039(98)02605-7

Reference yield:

: 88476-93-1
10-undecen-1-ylmagnesium bromide

: 220831-08-3
(3S,4R,5R)-3,4-Bis-benzyloxy-5-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: 2.) Et₃SiH, BF₃*OEt₂ / 1.) THF, r.t.; 2.) CH₂Cl₂, -78 deg C to -50 deg C

2: 99 percent / OsO₄, NMO / acetone; H₂O

3: NaIO₄ / diethyl ether; H₂O

4: tetrahydrofuran / 0 °C

5: 90 percent / PCC, MS 4A / CH₂Cl₂

6: 92 percent / Bu₄NF / tetrahydrofuran

7: 100 percent / Ag₂O / ethyl acetate

8: 70 percent / CAN / acetonitrile

9: 96 percent / p-TsOH / benzene / Heating

With triethylsilane; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; pyridinium chlorochromate; silver(l) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; ethyl acetate; acetone; acetonitrile; benzene;
DOI:10.1016/S0040-4039(98)02605-7