Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-triisopropylsilanyloxy-propyl)-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-triisopropylsilanyloxy-propyl)-tetrahydro-pyran-3-yl ester
• CAS No.: 440362-88-9
• Molecular Formula: C₄₁H₅₈O₇Si
• Molecular Weight: 690.993
• Mol file: 440362-88-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 2 articles about Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-triisopropylsilanyloxy-propyl)-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: 69.0%

triisopropylsilyl chloride (13154-24-0) + Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester (440362-96-9) → Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-triisopropylsilanyloxy-propyl)-tetrahydro-pyran-3-yl ester (440362-88-9)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1016/S0040-4020(02)00057-1

Reference yield:

3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)propene (193546-84-8) → Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-triisopropylsilanyloxy-propyl)-tetrahydro-pyran-3-yl ester (440362-88-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BH₃ / tetrahydrofuran / 2 h / 0 °C

1.2: 73 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / 0 - 20 °C

2.1: 69 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 5 h / 20 °C

With dmap; borane; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4020(02)00057-1

Reference yield: 81.0%

Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-triisopropylsilanyloxy-propyl)-tetrahydro-pyran-3-yl ester (440362-88-9) + 1,1-dibromomethane (74-95-3) → [3-(4,5-bis-benzyloxy-6-benzyloxymethyl-3-isopropenyloxy-terahydro-pyran-2-yl)-propoxy]-triisopropylsilane

Guidance literature:

With titanium tetrachloride; zinc; In tetrahydrofuran; dichloromethane; at 65 ℃; for 4.5h;

DOI:10.1016/S0040-4020(02)00057-1

upstream raw materials:

triisopropylsilyl chloride

Acetic acid (2S,3S,4S,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-(3-hydroxy-propyl)-tetrahydro-pyran-3-yl ester

3-C-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glycopyranosyl)propene