1,3,4,5-Tetra-O-benzyl-6-O-(tert-butyldimethylsilyl)-L-galactitol

Base Information

• Chemical Name: 1,3,4,5-Tetra-O-benzyl-6-O-(tert-butyldimethylsilyl)-L-galactitol
• CAS No.: 158535-90-1
• Molecular Formula: C₄₀H₅₂O₆Si
• Molecular Weight: 656.935
• Mol file: 158535-90-1.mol

Synonyms:1,3,4,5-Tetra-O-benzyl-6-O-(tert-butyldimethylsilyl)-L-galactitol

Chemical Property of 1,3,4,5-Tetra-O-benzyl-6-O-(tert-butyldimethylsilyl)-L-galactitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3,4,5-Tetra-O-benzyl-6-O-(tert-butyldimethylsilyl)-L-galactitol

There total 5 articles about 1,3,4,5-Tetra-O-benzyl-6-O-(tert-butyldimethylsilyl)-L-galactitol 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: 94.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 2,3,4,6-tetra-O-benzyl-D-galactitol (158570-84-4) → 1,3,4,5-Tetra-O-benzyl-6-O-(tert-butyldimethylsilyl)-L-galactitol (158535-90-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 22h;

DOI:10.1021/ol0631408

Reference yield:

2,3,4,6-tetra-O-benzyl-α-D-galactopyranose (4132-28-9,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4291-69-4) → 1,3,4,5-Tetra-O-benzyl-6-O-(tert-butyldimethylsilyl)-L-galactitol (158535-90-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / NaBH₄ / methanol / 2 h / 20 °C

2: 94 percent / Et₃N; DMAP / CH₂Cl₂ / 22 h / 20 °C

With dmap; sodium tetrahydroborate; triethylamine; In methanol; dichloromethane;

DOI:10.1021/ol0631408

Reference yield:

benzyl chloride (100-44-7) → 1,3,4,5-Tetra-O-benzyl-6-O-(tert-butyldimethylsilyl)-L-galactitol (158535-90-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / NaH / 130 °C

2: 76 percent / AcOH; H₂SO₄ / 85 °C

3: 73 percent / NaBH₄ / methanol / 2 h / 20 °C

4: 94 percent / Et₃N; DMAP / CH₂Cl₂ / 22 h / 20 °C

With dmap; sodium tetrahydroborate; sulfuric acid; sodium hydride; acetic acid; triethylamine; In methanol; dichloromethane;

DOI:10.1021/ol0631408

upstream raw materials:

tert-butyldimethylsilyl chloride

2,3,4,6-tetra-O-benzyl-D-galactitol

2,3,4,6-tetra-O-benzyl-α-D-galactopyranose

benzyl chloride

Downstream raw materials:

tert-Butyl-dimethyl-((Z)-(2S,3S,4S)-2,3,4-tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-enyloxy)-silane

(Z)-(2S,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-en-1-ol

(1R,4S,5S,6S)-4,5,6-tribenzyloxy-3-((benzyloxy)methyl)-cyclohex-2-enol

(Z)-(2R,3S,4S)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-6-bromo-hex-5-enal