3,4,6-tri-O-acetyl-1,2-O-<1-(endo-cyano)-ethylidene>-α-D-galactopyranose

Base Information

• Chemical Name: 3,4,6-tri-O-acetyl-1,2-O-<1-(endo-cyano)-ethylidene>-α-D-galactopyranose
• CAS No.: 69927-14-6
• Molecular Formula: C₁₅H₁₉NO₉
• Molecular Weight: 357.317
• Mol file: 69927-14-6.mol

Synonyms:3,4,6-tri-O-acetyl-1,2-O-<1-(endo-cyano)-ethylidene>-α-D-galactopyranose

Chemical Property of 3,4,6-tri-O-acetyl-1,2-O-<1-(endo-cyano)-ethylidene>-α-D-galactopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,6-tri-O-acetyl-1,2-O-<1-(endo-cyano)-ethylidene>-α-D-galactopyranose

There total 2 articles about 3,4,6-tri-O-acetyl-1,2-O-<1-(endo-cyano)-ethylidene>-α-D-galactopyranose 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: 59.7%

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(5,5-dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester (68579-18-0) + trimethylsilyl cyanide (7677-24-9) → 3,4,6-tri-O-acetyl-1,2-O-<1-(exo-cyano)ethylidene>-α-D-galactopyranose (69927-13-5) + 3,4,6-tri-O-acetyl-1,2-O-<1-(endo-cyano)-ethylidene>-α-D-galactopyranose (69927-14-6) + 5,5-Dimethyl-2-trimethylsilanyloxy-[1,3,2]dioxaphosphinane 2-sulfide (115010-70-3) + 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptonitrile (52443-07-9)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In acetonitrile; at 20 ℃; for 4h;

DOI:10.1016/S0008-6215(00)00216-0

Reference yield: 42.8%

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(5,5-dimethyl-2-oxo-2λ5-[1,3,2]dioxaphosphinan-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester (194546-40-2) + trimethylsilyl cyanide (7677-24-9) → 3,4,6-tri-O-acetyl-1,2-O-<1-(exo-cyano)ethylidene>-α-D-galactopyranose (69927-13-5) + 3,4,6-tri-O-acetyl-1,2-O-<1-(endo-cyano)-ethylidene>-α-D-galactopyranose (69927-14-6) + 5,5-Dimethyl-2-trimethylsilanyloxy-[1,3,2]dioxaphosphinane 2-sulfide (115010-70-3) + 3,4,5,7-tetra-O-acetyl-2,6-anhydro-D-glycero-L-manno-heptonitrile (52443-07-9)

Guidance literature:

With 4 A molecular sieve; boron trifluoride diethyl etherate; In acetonitrile; at 20 ℃; for 25h;

DOI:10.1016/S0008-6215(00)00216-0

Reference yield: 84.0%

3,4,6-tri-O-acetyl-1,2-O-<1-(endo-cyano)-ethylidene>-α-D-galactopyranose (69927-14-6) + 2-((2R,3R,4R,5S,6R)-4-Benzyloxy-2-methoxy-5-trityloxy-6-trityloxymethyl-tetrahydro-pyran-3-yl)-isoindole-1,3-dione → Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-4-benzyloxy-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester

Guidance literature:

With triphenylmethyl perchlorate; In dichloromethane;

DOI:10.1016/S0040-4039(00)61529-0

upstream raw materials:

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester

trimethylsilyl cyanide

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(5,5-dimethyl-2-oxo-2λ⁵-[1,3,2]dioxaphosphinan-2-ylsulfanyl)-tetrahydro-pyran-3-yl ester

Downstream raw materials:

Methyl-2,3-O-isopropyliden-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-L-rhamnopyranosid

2,2,2-triphenylacetonitrile

methyl 2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-L-rhamnopyranoside

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((2R,3R,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-2-trityloxymethyl-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-3-yl ester