2-Trimethylsilanyl-ethanesulfonic acid [(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]-amide

Base Information

• Chemical Name: 2-Trimethylsilanyl-ethanesulfonic acid [(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]-amide
• CAS No.: 183989-08-4
• Molecular Formula: C₆₁H₇₄N₂O₁₀SSi
• Molecular Weight: 1055.42
• Mol file: 183989-08-4.mol

Synonyms:2-Trimethylsilanyl-ethanesulfonic acid [(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]-amide

Chemical Property of 2-Trimethylsilanyl-ethanesulfonic acid [(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]-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Trimethylsilanyl-ethanesulfonic acid [(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]-amide

There total 5 articles about 2-Trimethylsilanyl-ethanesulfonic acid [(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]-amide 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: 49.0%

(4aS,6R,7R,7aR)-5-Benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-ol (183988-98-9) + 2-Trimethylsilanyl-ethanesulfonic acid ((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-iodo-tetrahydro-pyran-2-yl)-amide (183989-07-3) → 2-Trimethylsilanyl-ethanesulfonic acid [(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]-amide (183989-08-4)

Guidance literature:

With 2,2,6,6-tetramethylpiperidinyl-lithium; silver trifluoromethanesulfonate; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/ja960526c

Reference yield:

3,4,6-tri-O-benzyl-D-glucal (55628-54-1) → 2-Trimethylsilanyl-ethanesulfonic acid [(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]-amide (183989-08-4)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With iodonium(di-γ-collidine) perchlorate; 4 A molecular sieve; 2,2,6,6-tetramethylpiperidinyl-lithium; silver trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja960526c

Reference yield:

benzyl bromide (100-39-0) → 2-Trimethylsilanyl-ethanesulfonic acid [(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]-amide (183989-08-4)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 2,2,6,6-tetramethylpiperidinyl-lithium; silver trifluoromethanesulfonate; di(n-butyl)tin oxide; cesium fluoride; In tetrahydrofuran;

DOI:10.1021/ja960526c

upstream raw materials:

(4aS,6R,7R,7aR)-5-Benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-ol

2-Trimethylsilanyl-ethanesulfonic acid ((2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-iodo-tetrahydro-pyran-2-yl)-amide

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

benzyl bromide

Downstream 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

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