(3S,4R,5R)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-hydroxymethyl-2-pyrrolidinone

Base Information

• Chemical Name: (3S,4R,5R)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-hydroxymethyl-2-pyrrolidinone
• CAS No.: 190902-23-9
• Molecular Formula: C₁₇H₂₅NO₇
• Molecular Weight: 355.388
• Mol file: 190902-23-9.mol

Synonyms:(3S,4R,5R)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-hydroxymethyl-2-pyrrolidinone

Chemical Property of (3S,4R,5R)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-hydroxymethyl-2-pyrrolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5R)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-hydroxymethyl-2-pyrrolidinone

There total 8 articles about (3S,4R,5R)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-hydroxymethyl-2-pyrrolidinone 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: 46.0%

(3S,4R,5RS)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-methoxycarbonyl-2-pyrrolidinone (190902-22-8) → (3S,4R,5S)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-hydroxymethyl-2-pyrrolidinone (190902-34-2) + (3S,4R,5R)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-hydroxymethyl-2-pyrrolidinone (190902-23-9)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 20 ℃; for 20h;

DOI:10.1016/S0040-4020(99)00459-7

Reference yield:

(2S,3R)-2,3-bis(methoxymethoxy)-4-<(t-butyldimethylsilyl)oxy>butanal (166542-99-0) → (3S,4R,5R)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-hydroxymethyl-2-pyrrolidinone (190902-23-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / tetrahydrofuran / 1 h / 20 °C

2: 87 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

3: NMO; TPAP / CH₂Cl₂ / 1 h / Heating

4: methanol / 0.5 h

5: 46 percent / LiBH₄ / tetrahydrofuran / 20 h / 20 °C

With lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; In tetrahydrofuran; methanol; dichloromethane; 1: Condensation / 2: Substitution / 3: Cyclization / 4: Hydrolysis / 5: Reduction;

DOI:10.1016/S0040-4020(99)00459-7

Reference yield:

(3S,4R,5RS)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-cyano-2-pyrrolidinone (190902-21-7) → (3S,4R,5R)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-hydroxymethyl-2-pyrrolidinone (190902-23-9)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol / 0.5 h

2: 46 percent / LiBH₄ / tetrahydrofuran / 20 h / 20 °C

With lithium borohydride; In tetrahydrofuran; methanol; 1: Hydrolysis / 2: Reduction;

DOI:10.1016/S0040-4020(99)00459-7

upstream raw materials:

(3S,4R,5RS)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-methoxycarbonyl-2-pyrrolidinone

4-methoxy-benzylamine

(2S,3R)-2,3-bis(methoxymethoxy)-4-<(t-butyldimethylsilyl)oxy>butanal

(1RS,2S,3R)-2,3-bis(methoxymethyl)oxy-4-hydroxy-1-cyano-N-(4-methoxybenzyl)butanamide

Downstream raw materials:

(3S,4R,5R)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)-2-pyrrolidinone

(2R,3R,4R)-2-hydroxymethyl-3,4-dihydro-2H-pyrrole-3,4-diol

(3S,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)pyrrolidin-2-one

(3S,4R,5R)-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)-2-pyrrolidinone