((2S,3R,4R,5R)-1-Acetyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-ylmethyl)-phosphonic acid monoicosyl ester

Base Information

Chemical Name:((2S,3R,4R,5R)-1-Acetyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-ylmethyl)-phosphonic acid monoicosyl ester
CAS No.:397242-84-1
Molecular Formula:C₄₉H₇₄NO₇P
Molecular Weight:820.103
Hs Code.:

Synonyms:((2S,3R,4R,5R)-1-Acetyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-ylmethyl)-phosphonic acid monoicosyl ester

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Chemical Property of ((2S,3R,4R,5R)-1-Acetyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-ylmethyl)-phosphonic acid monoicosyl ester

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Technology Process of ((2S,3R,4R,5R)-1-Acetyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-ylmethyl)-phosphonic acid monoicosyl ester

There total 8 articles about ((2S,3R,4R,5R)-1-Acetyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-ylmethyl)-phosphonic acid monoicosyl 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: 76.0%

: 629-96-9
n-eicosanol

: 397242-83-0
((2S,3R,4R,5R)-1-Acetyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-ylmethyl)-phosphonic acid dimethyl ester

: 397242-84-1
((2S,3R,4R,5R)-1-Acetyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-ylmethyl)-phosphonic acid monoicosyl ester

Guidance literature:: ((2S,3R,4R,5R)-1-Acetyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-ylmethyl)-phosphonic acid dimethyl ester; With trimethylsilyl bromide; In dichloromethane; at 0 - 20 ℃; for 16h;

With triethylamine; In methanol; at 20 ℃; for 0.166667h;

n-eicosanol; With trichloroacetonitrile; In pyridine; at 70 ℃; for 16h;
DOI:10.1016/S0040-4039(01)01684-7

Reference yield:

: 397242-80-7
(2R,3R,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-3,4-dihydro-2H-pyrrole

: 397242-84-1
((2S,3R,4R,5R)-1-Acetyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-ylmethyl)-phosphonic acid monoicosyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 32 percent / BF₃*OEt₂ / tetrahydrofuran / 2 h / -78 - 20 °C

2.1: 61 percent / pyridine / 16 h / 20 °C

3.1: TMSBr / CH₂Cl₂ / 16 h / 0 - 20 °C

3.2: NEt₃ / methanol / 0.17 h / 20 °C

3.3: 76 percent / trichloroacetonitrile / pyridine / 16 h / 70 °C

With trimethylsilyl bromide; boron trifluoride diethyl etherate; In tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1016/S0040-4039(01)01684-7

Reference yield:

: (1R,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-pent-4-enylamine

: 397242-84-1
((2S,3R,4R,5R)-1-Acetyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidin-2-ylmethyl)-phosphonic acid monoicosyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: triethylamine / 2 h / 0 - 20 °C

2.1: NMO; OsO₄ / tetrahydrofuran; acetone; H₂O / 48 h / 20 °C

3.1: NaIO₄ / tetrahydrofuran; acetone; H₂O / 1.5 h / 20 °C

4.1: 86 percent / LiOH / tetrahydrofuran; methanol; H₂O / 2 h / 20 °C

5.1: 32 percent / BF₃*OEt₂ / tetrahydrofuran / 2 h / -78 - 20 °C

6.1: 61 percent / pyridine / 16 h / 20 °C

7.1: TMSBr / CH₂Cl₂ / 16 h / 0 - 20 °C

7.2: NEt₃ / methanol / 0.17 h / 20 °C

7.3: 76 percent / trichloroacetonitrile / pyridine / 16 h / 70 °C

With lithium hydroxide; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; trimethylsilyl bromide; boron trifluoride diethyl etherate; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; triethylamine; acetone;
DOI:10.1016/S0040-4039(01)01684-7