(2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol

Base Information

• Chemical Name: (2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol
• CAS No.: 335275-41-7
• Molecular Formula: C₅₅H₆₈O₁₁Si
• Molecular Weight: 933.224
• Mol file: 335275-41-7.mol

Synonyms:(2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol

Chemical Property of (2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol

There total 1 articles about (2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol 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: 87.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol (172147-75-0) → (2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol (335275-41-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 16h;

DOI:10.1016/S0960-894X(00)00692-2

Reference yield: 60.0%

benzyl (R)-(+)-3-phenyl-2-(trifluoromethylsulfonyloxy)propanoate (111437-25-3) + (2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol (335275-41-7) → (S)-2-{(2R,3S,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3,5-dihydroxy-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-3-phenyl-propionic acid benzyl ester (335275-42-8)

Guidance literature:

(2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol; With di(n-butyl)tin oxide; In methanol; for 2h; Heating;

benzyl (R)-3-phenyl-2-trifluoromethanesulfonyloxy-propionate; With cesium fluoride; In 1,2-dimethoxyethane; for 24h;

DOI:10.1016/S0960-894X(00)00692-2

Reference yield:

(2R,3R,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol (335275-41-7) → (S)-2-{(2S,3R,4S,5R,6R)-2-Carbamoyl-3,5-dihydroxy-6-[(1R,2R)-2-((2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-3-cyclohexyl-propionic acid

Guidance literature:

Multi-step reaction with 8 steps

1.1: Bu₂SnO / methanol / 2 h / Heating

1.2: CsF / 1,2-dimethoxy-ethane / 24 h

2.1: 87 percent / pyridine / CH₂Cl₂ / 0.17 h

3.1: 65 percent / TBAF; AcOH / tetrahydrofuran / 16 h

4.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

5.1: aq. NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / propan-2-ol / 16 h / 20 °C

6.1: Dowex WX₈H⁺-form

6.2: (CH₃)2C=CClN(CH₃)2 / CH₂Cl₂ / 1 h / 0 °C

6.3: 75 percent / aq. NH₃ / tetrahydrofuran / 5 h

7.1: 83 percent / H₂NCSNH₂ / ethanol / 48 h / 50 °C

8.1: 90 percent / H₂ / Pd(OH)2/C / dioxane; H₂O / 3 h

With pyridine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; Dowex WX₈H⁺-form; tetrabutyl ammonium fluoride; hydrogen; di(n-butyl)tin oxide; Dess-Martin periodane; acetic acid; thiourea; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; isopropyl alcohol;

DOI:10.1016/S0960-894X(00)00692-2

upstream raw materials:

tert-butylchlorodiphenylsilane

(2R,3R,4S,5R,6R)-2-Hydroxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-3,4,5-triol

Downstream raw materials:

(S)-2-{(2R,3S,4S,5R,6R)-2-(tert-Butyl-diphenyl-silanyloxymethyl)-3,5-dihydroxy-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-3-phenyl-propionic acid benzyl ester

(S)-2-{(2R,3S,4S,5R,6R)-3,5-Dihydroxy-2-hydroxymethyl-6-[(1R,2R)-2-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyloxy]-tetrahydro-pyran-4-yloxy}-3-phenyl-propionic acid benzyl ester