Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-ethylsulfanyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-ethylsulfanyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester
CAS No.:196704-16-2
Molecular Formula:C₃₃H₅₀O₆SSi
Molecular Weight:602.908
Hs Code.:

Synonyms:Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-ethylsulfanyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

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Chemical Property of Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-ethylsulfanyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

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Technology Process of Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-ethylsulfanyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

There total 5 articles about Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-ethylsulfanyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester 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: 100.0%

: 108-24-7
acetic anhydride

: 196704-01-5
thioethyl 3,4-di-O-benzyl-6-O-triisopropylsilyl-β-D-mannopyranoside

: 196704-16-2
Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-ethylsulfanyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: With pyridine; dmap; In dichloromethane;
DOI:10.1021/ja971640d

Reference yield:

: 196703-95-4
1,5-anhydro-2-deoxy-3,4-di-O-benzyl-6-O-triisopropylsilyl-D-arabino-hex-1-enitol

: 196704-16-2
Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-ethylsulfanyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: dimethyldioxirane / CH₂Cl₂; acetone / 0.33 h / 0 °C

2: trifluoroacetic acid anhydride / CH₂Cl₂ / 0.33 h / -78 °C

3: Ac₂O; DMSO / 72 h / 20 °C

4: NaBH₄ / methanol; CH₂Cl₂ / 0 - 20 °C

5: 100 percent / pyridine; DMAP / CH₂Cl₂

With pyridine; dmap; sodium tetrahydroborate; 3,3-dimethyldioxirane; acetic anhydride; dimethyl sulfoxide; trifluoroacetic anhydride; In methanol; dichloromethane; acetone; 1: Epoxidation / 2: Ring cleavage / 3: Oxidation / 4: Reduction / 5: Acetylation;
DOI:10.1021/ja971640d

Reference yield:

: 328047-23-0
((1S,3R,4R,5S,6R)-4,5-Bis-benzyloxy-2,7-dioxa-bicyclo[4.1.0]hept-3-ylmethoxy)-triisopropyl-silane

: 196704-16-2
Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-2-ethylsulfanyl-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: trifluoroacetic acid anhydride / CH₂Cl₂ / 0.33 h / -78 °C

2: Ac₂O; DMSO / 72 h / 20 °C

3: NaBH₄ / methanol; CH₂Cl₂ / 0 - 20 °C

4: 100 percent / pyridine; DMAP / CH₂Cl₂

With pyridine; dmap; sodium tetrahydroborate; acetic anhydride; dimethyl sulfoxide; trifluoroacetic anhydride; In methanol; dichloromethane; 1: Ring cleavage / 2: Oxidation / 3: Reduction / 4: Acetylation;
DOI:10.1021/ja971640d