(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-5-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-5-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:220831-10-7
Molecular Formula:C₄₆H₆₅NO₈
Molecular Weight:760.024
Hs Code.:

(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-5-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-5-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-5-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 17 articles about (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-5-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl 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:

: (2R,3R,4R,5S)-3,4-Bis-benzyloxy-2-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-5-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 220831-10-7
(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-5-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With sodium tetrahydroborate; In methanol; Yield given;
DOI:10.1016/S0040-4039(98)02605-7

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 220831-10-7
(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-5-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / Et₃N, DMAP / CH₂Cl₂

2: 2.) NaBH₄, CeCl₃ / 1.) THF, -78 deg C; 2.) MeOH, -45 deg c

3: Et₃N / CH₂Cl₂

4: t-BuOK / tetrahydrofuran

5: 100 percent / OsO₄, NMO / acetone; H₂O

6: NaIO₄ / diethyl ether; H₂O

7: NaBH₄ / methanol

With dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; potassium tert-butylate; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone;
DOI:10.1016/S0040-4039(98)02605-7

Reference yield:

: 183312-54-1
3-benzyloxypropylmagnesium bromide

: 220831-10-7
(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-5-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 13 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

7: 100 percent / Et₃N, DMAP / CH₂Cl₂

8: 2.) NaBH₄, CeCl₃ / 1.) THF, -78 deg C; 2.) MeOH, -45 deg c

9: Et₃N / CH₂Cl₂

10: t-BuOK / tetrahydrofuran

11: 100 percent / OsO₄, NMO / acetone; H₂O

12: NaIO₄ / diethyl ether; H₂O

13: NaBH₄ / methanol

With dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; cerium(III) chloride; ammonium cerium(IV) nitrate; potassium tert-butylate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; triethylamine; pyridinium chlorochromate; silver(l) oxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; acetone; acetonitrile; benzene;
DOI:10.1016/S0040-4039(98)02605-7