(2S,3S,5R)-3,4,6-Tris-O-benzyl-1,2-O-isopropylidene-D-sorbitol

Base Information

• Chemical Name: (2S,3S,5R)-3,4,6-Tris-O-benzyl-1,2-O-isopropylidene-D-sorbitol
• CAS No.: 135284-42-3
• Molecular Formula: C₃₀H₃₆O₆
• Molecular Weight: 492.612
• Mol file: 135284-42-3.mol

Synonyms:(2S,3S,5R)-3,4,6-Tris-O-benzyl-1,2-O-isopropylidene-D-sorbitol

Chemical Property of (2S,3S,5R)-3,4,6-Tris-O-benzyl-1,2-O-isopropylidene-D-sorbitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5R)-3,4,6-Tris-O-benzyl-1,2-O-isopropylidene-D-sorbitol

There total 11 articles about (2S,3S,5R)-3,4,6-Tris-O-benzyl-1,2-O-isopropylidene-D-sorbitol 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: 76.0%

3,5,6-Tris-O-benzyl-D-sorbitol (135284-41-2) + acetone (67-64-1) → [(4S,5R,6R)-5-Benzyloxy-6-((R)-1,2-bis-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxan-4-yl]-methanol (135310-56-4) + (5S,6R,7R)-6-Benzyloxy-7-((R)-1,2-bis-benzyloxy-ethyl)-2,2-dimethyl-[1,3]dioxepan-5-ol (135284-43-4) + (2S,3S,5R)-3,4,6-Tris-O-benzyl-1,2-O-isopropylidene-D-sorbitol (135284-42-3)

Guidance literature:

With toluene-4-sulfonic acid; for 1h; Ambient temperature;

Reference yield: 70.0%

3,5,6-Tris-O-benzyl-D-sorbitol (135284-41-2) + 2,2-dimethoxy-propane (77-76-9) → (2S,3S,5R)-3,4,6-Tris-O-benzyl-1,2-O-isopropylidene-D-sorbitol (135284-42-3)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 2h;

DOI:10.1016/j.carres.2006.03.001

Reference yield:

1,2-O-isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranoside (53928-30-6) → (2S,3S,5R)-3,4,6-Tris-O-benzyl-1,2-O-isopropylidene-D-sorbitol (135284-42-3)

Guidance literature:

Multi-step reaction with 3 steps

1: p-toluenesulfonic acid / acetonitrile; H₂O

2: NaBH₄ / methanol

3: 70 percent / p-toluenesulfonic acid monohydrate / acetone / 2 h / 20 °C

With sodium tetrahydroborate; toluene-4-sulfonic acid; In methanol; water; acetone; acetonitrile;

DOI:10.1016/j.carres.2006.03.001

upstream raw materials:

3,5,6-Tris-O-benzyl-D-sorbitol

acetone

2,2-dimethoxy-propane

benzyl bromide

Downstream raw materials:

(2S,3S,5S)-3,5,6-Tris-O-benzyl-1,2-O-isopropylidene-1,2,3,5,6-hexane-pentol

3,4,5,6-tetra-O-benzyl-D-sorbitol

3,5,6-tri-O-benzyl-4-O-tosyl-D-glucitol

1,4-anhydro-3,5,6-tri-O-benzyl-D-tagatose diethyl acetal