(3S,4S,5R)-4,5-Bis-benzyloxy-3-benzyloxymethyl-hepta-1,6-dien-3-ol

Base Information

• Chemical Name: (3S,4S,5R)-4,5-Bis-benzyloxy-3-benzyloxymethyl-hepta-1,6-dien-3-ol
• CAS No.: 226225-94-1
• Molecular Formula: C₂₉H₃₂O₄
• Molecular Weight: 444.571
• Mol file: 226225-94-1.mol

Synonyms:(3S,4S,5R)-4,5-Bis-benzyloxy-3-benzyloxymethyl-hepta-1,6-dien-3-ol

Chemical Property of (3S,4S,5R)-4,5-Bis-benzyloxy-3-benzyloxymethyl-hepta-1,6-dien-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S,5R)-4,5-Bis-benzyloxy-3-benzyloxymethyl-hepta-1,6-dien-3-ol

There total 3 articles about (3S,4S,5R)-4,5-Bis-benzyloxy-3-benzyloxymethyl-hepta-1,6-dien-3-ol 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: 98.0%

vinyl magnesium bromide (1826-67-1) + (3S,4R)-1,3,4-tris(benzyloxy)-hex-5-en-2-one (220939-94-6) → (3S,4S,5R)-4,5-Bis-benzyloxy-3-benzyloxymethyl-hepta-1,6-dien-3-ol (226225-94-1)

Guidance literature:

In tetrahydrofuran; at -78 - 20 ℃; for 16h;

DOI:10.1016/S0040-4039(99)01141-7

Reference yield:

2,3,5-tri-O-benzyl-D-arabinofuranose (160549-10-0) → (3S,4S,5R)-4,5-Bis-benzyloxy-3-benzyloxymethyl-hepta-1,6-dien-3-ol (226225-94-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 87.6 percent / n-BuLi / tetrahydrofuran / 3 h / Heating

2: 87.2 percent / PCC / CH₂Cl₂

3: 96.2 percent / tetrahydrofuran / 3 h / -78 °C

With n-butyllithium; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; 1: Wittig reaction;

DOI:10.1016/j.tetasy.2007.08.033

Reference yield:

(3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene (102208-53-7) → (3S,4S,5R)-4,5-Bis-benzyloxy-3-benzyloxymethyl-hepta-1,6-dien-3-ol (226225-94-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 87.2 percent / PCC / CH₂Cl₂

2: 96.2 percent / tetrahydrofuran / 3 h / -78 °C

With pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetasy.2007.08.033

upstream raw materials:

vinyl magnesium bromide

(3S,4R)-1,3,4-tris(benzyloxy)-hex-5-en-2-one

2,3,5-tri-O-benzyl-D-arabinofuranose

(3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene

Downstream raw materials:

((1S,2S,3R)-2,3-Bis-benzyloxy-1-benzyloxymethyl-1-vinyl-pent-4-enyloxy)-trimethyl-silane

(1S,4R,5S)-4,5-Bis-benzyloxy-1-benzyloxymethyl-cyclopent-2-enol

C₃₆H₃₈O₄

2,5-anhydro-3,4,6-tri-O-benzyl-1-iodo-5-vinyl-L-mannohexitol