2-Trimethylsilanyl-ethanesulfonic acid [(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-amide

Base Information

• Chemical Name: 2-Trimethylsilanyl-ethanesulfonic acid [(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-amide
• CAS No.: 351209-67-1
• Molecular Formula: C₅₇H₇₃NO₁₁S₂Si
• Molecular Weight: 1040.42

Synonyms:2-Trimethylsilanyl-ethanesulfonic acid [(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-amide

Chemical Property of 2-Trimethylsilanyl-ethanesulfonic acid [(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-amide

Chemical Property:

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Technology Process of 2-Trimethylsilanyl-ethanesulfonic acid [(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-amide

There total 6 articles about 2-Trimethylsilanyl-ethanesulfonic acid [(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-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: 85.0%

2-Trimethylsilanyl-ethanesulfonic acid [(2R,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-iodo-tetrahydro-pyran-3-yl]-amide + ethanethiol (75-08-1) → 2-Trimethylsilanyl-ethanesulfonic acid [(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-amide (351209-67-1)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; at -40 - 20 ℃;

DOI:10.1016/j.tet.2006.02.080

Reference yield:

hexa-O-acetyl-D-lactal (51450-24-9) → 2-Trimethylsilanyl-ethanesulfonic acid [(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-amide (351209-67-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NH₃ / methanol

2.1: Bu₂SnO / benzene

2.2: Bu₄NBr

3.1: NaH / dimethylformamide / 0.5 h / 0 °C

3.2: 91 percent / dimethylformamide / 24 h / 20 °C

4.1: CH₂Cl₂ / 0.5 h / 20 °C

4.2: 75 percent / I₂; Ag(collidine)2ClO₄ / CH₂Cl₂ / 1.5 h / 0 °C

5.1: 85 percent / LiHMDS / dimethylformamide; tetrahydrofuran / -40 - 20 °C

With ammonia; sodium hydride; di(n-butyl)tin oxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/j.tet.2006.02.080

Reference yield:

benzyl bromide (100-39-0) → 2-Trimethylsilanyl-ethanesulfonic acid [(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-amide (351209-67-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 91 percent / dimethylformamide / 24 h / 20 °C

2.1: CH₂Cl₂ / 0.5 h / 20 °C

2.2: 75 percent / I₂; Ag(collidine)2ClO₄ / CH₂Cl₂ / 1.5 h / 0 °C

3.1: 85 percent / LiHMDS / dimethylformamide; tetrahydrofuran / -40 - 20 °C

With sodium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.02.080

upstream raw materials:

ethanethiol

hexa-O-acetyl-D-lactal

benzyl bromide

4-O-(3-O-allyl-β-D-galactopyranosyl)-D-arabino-hex-1-enitol

Downstream raw materials:

2-[(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

2-[(2S,3R,4R,5S,6R)-4-Benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-3,5-bis-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-yloxy)-2-ethylsulfanyl-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

(2S,3R,4R,5S,6R)-5-((2S,3R,4S,5S,6R)-4-Allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-4-benzyloxy-6-benzyloxymethyl-2-ethylsulfanyl-tetrahydro-pyran-3-ylamine

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