N-[(2R,3R,4R,5S,6R)-2-((2R,3R,4R,5S)-1-Benzhydryl-2-benzyloxymethyl-4-hydroxy-5-hydroxymethyl-pyrrolidin-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-acetamide

Base Information

• Chemical Name: N-[(2R,3R,4R,5S,6R)-2-((2R,3R,4R,5S)-1-Benzhydryl-2-benzyloxymethyl-4-hydroxy-5-hydroxymethyl-pyrrolidin-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-acetamide
• CAS No.: 183989-10-8
• Molecular Formula: C₅₅H₆₀N₂O₉
• Molecular Weight: 893.089
• Mol file: 183989-10-8.mol

Synonyms:N-[(2R,3R,4R,5S,6R)-2-((2R,3R,4R,5S)-1-Benzhydryl-2-benzyloxymethyl-4-hydroxy-5-hydroxymethyl-pyrrolidin-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-acetamide

Chemical Property of N-[(2R,3R,4R,5S,6R)-2-((2R,3R,4R,5S)-1-Benzhydryl-2-benzyloxymethyl-4-hydroxy-5-hydroxymethyl-pyrrolidin-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-acetamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-[(2R,3R,4R,5S,6R)-2-((2R,3R,4R,5S)-1-Benzhydryl-2-benzyloxymethyl-4-hydroxy-5-hydroxymethyl-pyrrolidin-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-acetamide

There total 9 articles about N-[(2R,3R,4R,5S,6R)-2-((2R,3R,4R,5S)-1-Benzhydryl-2-benzyloxymethyl-4-hydroxy-5-hydroxymethyl-pyrrolidin-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-acetamide 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: 82.0%

N-[(2R,3R,4R,5S,6R)-2-((4aS,6R,7R,7aR)-5-Benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-acetamide (183989-09-5) → N-[(2R,3R,4R,5S,6R)-2-((2R,3R,4R,5S)-1-Benzhydryl-2-benzyloxymethyl-4-hydroxy-5-hydroxymethyl-pyrrolidin-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-acetamide (183989-10-8)

Guidance literature:

With hydrogenchloride; In methanol;

DOI:10.1021/ja960526c

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → N-[(2R,3R,4R,5S,6R)-2-((2R,3R,4R,5S)-1-Benzhydryl-2-benzyloxymethyl-4-hydroxy-5-hydroxymethyl-pyrrolidin-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-acetamide (183989-10-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / iodonium di-sym-collidine perchlorate, 4-A sieves / CH₂Cl₂ / 0 °C

2: 49 percent / LTMP, AgOTf / tetrahydrofuran / -78 - 20 °C

3: CsF / dimethylformamide / 95 °C

4: pyridine

5: 82 percent / conc. aq. HCl / methanol

With pyridine; hydrogenchloride; iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; 2,2,6,6-tetramethylpiperidinyl-lithium; silver trifluoromethanesulfonate; cesium fluoride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja960526c

Reference yield:

benzyl bromide (100-39-0) → N-[(2R,3R,4R,5S,6R)-2-((2R,3R,4R,5S)-1-Benzhydryl-2-benzyloxymethyl-4-hydroxy-5-hydroxymethyl-pyrrolidin-3-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-acetamide (183989-10-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) Bu₂SnO, 2.) CsF / 1.) MeOH, reflux, 2.) DMF

2: 49 percent / LTMP, AgOTf / tetrahydrofuran / -78 - 20 °C

3: CsF / dimethylformamide / 95 °C

4: pyridine

5: 82 percent / conc. aq. HCl / methanol

With pyridine; hydrogenchloride; 2,2,6,6-tetramethylpiperidinyl-lithium; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; cesium fluoride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/ja960526c

upstream raw materials:

N-[(2R,3R,4R,5S,6R)-2-((4aS,6R,7R,7aR)-5-Benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-yloxy)-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-yl]-acetamide

3,4,6-tri-O-benzyl-D-glucal

benzyl bromide

(2S,3R,4R,5R)-1-Benzhydryl-2,5-bis-hydroxymethyl-pyrrolidine-3,4-diol