[(R)-10-[2-(3-Benzyloxy-propyl)-[1,3]dioxolan-2-yl]-1-((1R,2R,3S)-1,2-bis-benzyloxy-3-hydroxy-pent-4-enyl)-decyl]-carbamic acid tert-butyl ester

Base Information

Chemical Name:[(R)-10-[2-(3-Benzyloxy-propyl)-[1,3]dioxolan-2-yl]-1-((1R,2R,3S)-1,2-bis-benzyloxy-3-hydroxy-pent-4-enyl)-decyl]-carbamic acid tert-butyl ester
CAS No.:220831-01-6
Molecular Formula:C₄₇H₆₇NO₈
Molecular Weight:774.051
Hs Code.:

[(R)-10-[2-(3-Benzyloxy-propyl)-[1,3]dioxolan-2-yl]-1-((1R,2R,3S)-1,2-bis-benzyloxy-3-hydroxy-pent-4-enyl)-decyl]-carbamic acid tert-butyl ester

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Chemical Property of [(R)-10-[2-(3-Benzyloxy-propyl)-[1,3]dioxolan-2-yl]-1-((1R,2R,3S)-1,2-bis-benzyloxy-3-hydroxy-pent-4-enyl)-decyl]-carbamic acid tert-butyl ester

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Technology Process of [(R)-10-[2-(3-Benzyloxy-propyl)-[1,3]dioxolan-2-yl]-1-((1R,2R,3S)-1,2-bis-benzyloxy-3-hydroxy-pent-4-enyl)-decyl]-carbamic acid tert-butyl ester

There total 12 articles about [(R)-10-[2-(3-Benzyloxy-propyl)-[1,3]dioxolan-2-yl]-1-((1R,2R,3S)-1,2-bis-benzyloxy-3-hydroxy-pent-4-enyl)-decyl]-carbamic 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:

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

: 220831-01-6
[(R)-10-[2-(3-Benzyloxy-propyl)-[1,3]dioxolan-2-yl]-1-((1R,2R,3S)-1,2-bis-benzyloxy-3-hydroxy-pent-4-enyl)-decyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / Et₃N, DMAP / CH₂Cl₂

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

With dmap; sodium tetrahydroborate; cerium(III) chloride; triethylamine; In dichloromethane;
DOI:10.1016/S0040-4039(98)02605-7

Reference yield:

: 183312-54-1
3-benzyloxypropylmagnesium bromide

: 220831-01-6
[(R)-10-[2-(3-Benzyloxy-propyl)-[1,3]dioxolan-2-yl]-1-((1R,2R,3S)-1,2-bis-benzyloxy-3-hydroxy-pent-4-enyl)-decyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 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

With dmap; sodium tetrahydroborate; cerium(III) chloride; ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; triethylamine; 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

: 220831-01-6
[(R)-10-[2-(3-Benzyloxy-propyl)-[1,3]dioxolan-2-yl]-1-((1R,2R,3S)-1,2-bis-benzyloxy-3-hydroxy-pent-4-enyl)-decyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 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

10: 100 percent / Et₃N, DMAP / CH₂Cl₂

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

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