(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-5-(1,2-dihydroxy-ethyl)-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-(1,2-dihydroxy-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:220831-09-4
Molecular Formula:C₄₇H₆₇NO₉
Molecular Weight:790.05
Hs Code.:

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

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

There total 15 articles about (2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-5-(1,2-dihydroxy-ethyl)-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: 100.0%

: 220831-02-7
(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-5-vinyl-pyrrolidine-1-carboxylic acid tert-butyl ester

: 220831-09-4
(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-5-(1,2-dihydroxy-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; In water; acetone;
DOI:10.1016/S0040-4039(98)02605-7

Reference yield:

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

: 220831-09-4
(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-5-(1,2-dihydroxy-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 183312-54-1
3-benzyloxypropylmagnesium bromide

: 220831-09-4
(2R,3R,4R,5R)-3,4-Bis-benzyloxy-2-{9-[2-(3-benzyloxy-propyl)-[1,3]dioxolan-2-yl]-nonyl}-5-(1,2-dihydroxy-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 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

With dmap; sodium tetrahydroborate; 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; dichloromethane; water; ethyl acetate; acetone; acetonitrile; benzene;
DOI:10.1016/S0040-4039(98)02605-7