O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-6-O-benzyl-3-deoxy-2-O-pivaloyl-α-D-glucopyranosyl 4,6-O-(R)-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranoside

Base Information

• Chemical Name: O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-6-O-benzyl-3-deoxy-2-O-pivaloyl-α-D-glucopyranosyl 4,6-O-(R)-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranoside
• CAS No.: 195135-19-4
• Molecular Formula: C₆₇H₉₀O₃₀
• Molecular Weight: 1375.43
• Mol file: 195135-19-4.mol

Synonyms:

Chemical Property of O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-6-O-benzyl-3-deoxy-2-O-pivaloyl-α-D-glucopyranosyl 4,6-O-(R)-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-6-O-benzyl-3-deoxy-2-O-pivaloyl-α-D-glucopyranosyl 4,6-O-(R)-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranoside

There total 6 articles about O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-6-O-benzyl-3-deoxy-2-O-pivaloyl-α-D-glucopyranosyl 4,6-O-(R)-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranoside 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: 42.0%

2,2-Dimethyl-propionic acid (2R,4aR,6R,7R,8S,8aR)-6-[(2R,3R,5S,6R)-6-benzyloxymethyl-3-(2,2-dimethyl-propionyloxy)-5-hydroxy-tetrahydro-pyran-2-yloxy]-7-(2,2-dimethyl-propionyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester (195135-17-2) + 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide (4753-07-5,5160-10-1,14206-57-6,14227-66-8,14257-35-3,42385-75-1,67650-37-7,68682-05-3,69308-57-2,69349-74-2,70223-96-0,70223-97-1,71276-38-5,85248-99-3,118493-15-5,120575-76-0) → O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-6-O-benzyl-3-deoxy-2-O-pivaloyl-α-D-glucopyranosyl 4,6-O-(R)-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranoside (195135-19-4)

Guidance literature:

With silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane; for 18h; Ambient temperature;

Reference yield:

pivaloyl chloride (3282-30-2) → O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-6-O-benzyl-3-deoxy-2-O-pivaloyl-α-D-glucopyranosyl 4,6-O-(R)-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranoside (195135-19-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 51 percent / CH₂Cl₂; pyridine / 1.) 0-5 deg C, 2 h, 2.) room temperature, overnight

2: 97 percent / DMAP / acetonitrile / 20 h / Heating

3: 84 percent / AIBN, Bu₃SnH / toluene / 16 h / Heating

4: 51 percent / NaBH₃CN, molecular sieves, HCl / tetrahydrofuran; diethyl ether / 0 °C

5: 42 percent / AgOTf, tetramethylurea / CH₂Cl₂ / 18 h / Ambient temperature

With hydrogenchloride; dmap; molecular sieve; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; silver trifluoromethanesulfonate; sodium cyanoborohydride; tetramethylurea; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; toluene; acetonitrile;

Reference yield:

4,6;4',6'-di-O-benzylidene-α,α-D-trehalose (18929-82-3,60949-45-3,97390-02-8,127128-52-3) → O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-O-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-6-O-benzyl-3-deoxy-2-O-pivaloyl-α-D-glucopyranosyl 4,6-O-(R)-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranoside (195135-19-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 51 percent / CH₂Cl₂; pyridine / 1.) 0-5 deg C, 2 h, 2.) room temperature, overnight

2: 97 percent / DMAP / acetonitrile / 20 h / Heating

3: 84 percent / AIBN, Bu₃SnH / toluene / 16 h / Heating

4: 51 percent / NaBH₃CN, molecular sieves, HCl / tetrahydrofuran; diethyl ether / 0 °C

5: 42 percent / AgOTf, tetramethylurea / CH₂Cl₂ / 18 h / Ambient temperature

With hydrogenchloride; dmap; molecular sieve; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; silver trifluoromethanesulfonate; sodium cyanoborohydride; tetramethylurea; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane; toluene; acetonitrile;

upstream raw materials:

2,2-Dimethyl-propionic acid (2R,4aR,6R,7R,8S,8aR)-6-[(2R,3R,5S,6R)-6-benzyloxymethyl-3-(2,2-dimethyl-propionyloxy)-5-hydroxy-tetrahydro-pyran-2-yloxy]-7-(2,2-dimethyl-propionyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yl ester

2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide

pivaloyl chloride

4,6;4',6'-di-O-benzylidene-α,α-D-trehalose

Downstream raw materials:

C₃₈H₅₂O₂₀