2,2-Dimethyl-propionic acid (2R,3R,4S,5R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2,4-bis-benzyloxy-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3R,4S,5R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2,4-bis-benzyloxy-tetrahydro-pyran-3-yl ester
• CAS No.: 144985-27-3
• Molecular Formula: C₅₄H₆₂O₁₁
• Molecular Weight: 887.08
• Mol file: 144985-27-3.mol

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3R,4S,5R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2,4-bis-benzyloxy-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2R,3R,4S,5R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2,4-bis-benzyloxy-tetrahydro-pyran-3-yl ester

There total 12 articles about 2,2-Dimethyl-propionic acid (2R,3R,4S,5R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2,4-bis-benzyloxy-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:

pivaloyl chloride (3282-30-2) → 2,2-Dimethyl-propionic acid (2R,3R,4S,5R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2,4-bis-benzyloxy-tetrahydro-pyran-3-yl ester (144985-27-3)

Guidance literature:

Multi-step reaction with 3 steps

2: 75 percent / silver triflate, MS₄A / CH₂Cl₂; toluene / -50 °C

3: 1) LiOH, 30percent H₂O₂, 2) KI, Ag₂O / 1) THF, 2) DMF

With lithium hydroxide; dihydrogen peroxide; silver trifluoromethanesulfonate; potassium iodide; silver(l) oxide; In dichloromethane; toluene;

DOI:10.1016/S0040-4039(00)61200-5

Reference yield:

4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (2872-65-3,14581-81-8,17042-40-9,84380-06-3,105260-62-6) → 2,2-Dimethyl-propionic acid (2R,3R,4S,5R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2,4-bis-benzyloxy-tetrahydro-pyran-3-yl ester (144985-27-3)

Guidance literature:

Multi-step reaction with 9 steps

1: NaOMe / methanol; tetrahydrofuran

2: 1) Bu₂SnO, 2) Bu₄NBr / 1) THF, toluene, 2) THF

3: TsOH*H₂O / tetrahydrofuran

4: DMAP, pyridine

5: 1) NaBH₃CN, powdered molecular sieves 4A, HCl, 2) NaH / 1) THF, 2) DMF

7: CCl₄, (Me₂N)3P / THF

8: 75 percent / silver triflate, MS₄A / CH₂Cl₂; toluene / -50 °C

9: 1) LiOH, 30percent H₂O₂, 2) KI, Ag₂O / 1) THF, 2) DMF

With pyridine; hydrogenchloride; tetrachloromethane; dmap; lithium hydroxide; 4 A molecular sieve; tetrabutylammomium bromide; dihydrogen peroxide; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; di(n-butyl)tin oxide; sodium cyanoborohydride; toluene-4-sulfonic acid; potassium iodide; silver(l) oxide; Hexamethylphosphorous triamide; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1016/S0040-4039(00)61200-5

Reference yield:

p-methoxyphenyl 3-O-allyl-β-D-galactopyranoside (144985-19-3) → 2,2-Dimethyl-propionic acid (2R,3R,4S,5R)-5-((2S,3R,4S,5S,6R)-4-allyloxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2,4-bis-benzyloxy-tetrahydro-pyran-3-yl ester (144985-27-3)

Guidance literature:

Multi-step reaction with 7 steps

1: TsOH*H₂O / tetrahydrofuran

2: DMAP, pyridine

3: 1) NaBH₃CN, powdered molecular sieves 4A, HCl, 2) NaH / 1) THF, 2) DMF

5: CCl₄, (Me₂N)3P / THF

6: 75 percent / silver triflate, MS₄A / CH₂Cl₂; toluene / -50 °C

7: 1) LiOH, 30percent H₂O₂, 2) KI, Ag₂O / 1) THF, 2) DMF

With pyridine; hydrogenchloride; tetrachloromethane; dmap; lithium hydroxide; 4 A molecular sieve; dihydrogen peroxide; silver trifluoromethanesulfonate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; potassium iodide; silver(l) oxide; Hexamethylphosphorous triamide; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/S0040-4039(00)61200-5

upstream raw materials:

benzyl bromide

2,2-Dimethyl-propionic acid (2R,3R,4S,5R)-5-((2S,3R,4S,5S,6R)-3-acetoxy-4-allyloxy-5-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2,4-bis-benzyloxy-tetrahydro-pyran-3-yl ester

4-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

pivaloyl chloride

Downstream raw materials:

Acetic acid (4aR,6S,7R,8S,8aS)-8-allyloxy-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

(4aR,6S,7R,8S,8aR)-7-Benzyloxy-6-[(2R,3S,4S,5R,6S)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-((3R,4S,5R,6R)-4,5,6-tris-benzyloxy-tetrahydro-pyran-3-yloxy)-tetrahydro-pyran-4-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol

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

Refernces