(3aR,5R,5aS,8aS,8bR)-5-[(3aS,4R,6S,7R,7aS)-7-(4-Methoxy-benzyloxy)-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran

Base Information

• Chemical Name: (3aR,5R,5aS,8aS,8bR)-5-[(3aS,4R,6S,7R,7aS)-7-(4-Methoxy-benzyloxy)-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran
• CAS No.: 143535-90-4
• Molecular Formula: C₃₇H₅₀O₁₃
• Molecular Weight: 702.796
• Mol file: 143535-90-4.mol

Synonyms:

Chemical Property of (3aR,5R,5aS,8aS,8bR)-5-[(3aS,4R,6S,7R,7aS)-7-(4-Methoxy-benzyloxy)-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,5R,5aS,8aS,8bR)-5-[(3aS,4R,6S,7R,7aS)-7-(4-Methoxy-benzyloxy)-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran

There total 10 articles about (3aR,5R,5aS,8aS,8bR)-5-[(3aS,4R,6S,7R,7aS)-7-(4-Methoxy-benzyloxy)-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran 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: 21.4%

(3aS,4R,6R,7R,7aS)-7-(4-Methoxy-benzyloxy)-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-6-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran (143535-86-8) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → (3aR,5R,5aS,8aS,8bR)-5-[(3aS,4R,6R,7R,7aS)-7-(4-Methoxy-benzyloxy)-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran (143535-91-5) + (3aR,5R,5aS,8aS,8bR)-5-[(3aS,4R,6S,7R,7aS)-7-(4-Methoxy-benzyloxy)-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran (143535-90-4)

Guidance literature:

With iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 A molecular sieve; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1016/0008-6215(91)80023-G

Reference yield:

methyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside (55663-79-1) → (3aR,5R,5aS,8aS,8bR)-5-[(3aS,4R,6S,7R,7aS)-7-(4-Methoxy-benzyloxy)-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran (143535-90-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 78.6 percent / NaH / dimethylformamide

2: CuBr₂, Bu₄NBr, 4 Angstroem molecular sieves / 1,2-dichloro-ethane; dimethylformamide / Ambient temperature

With 4 A molecular sieve; tetrabutylammomium bromide; sodium hydride; copper(ll) bromide; In 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(91)80023-G

Reference yield:

(3aS,4R,6R,7R,7aR)-4-Hydroxymethyl-2,2-dimethyl-6-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol (143535-85-7) → (3aR,5R,5aS,8aS,8bR)-5-[(3aS,4R,6S,7R,7aS)-7-(4-Methoxy-benzyloxy)-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran (143535-90-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / dimethylformamide

2: 4 Angstroem molecular sieves, iodonium di(2,4,6-trimethylpyridine) perchlorate / diethyl ether; CH₂Cl₂ / 2 h / Ambient temperature

With iodonium di(2,4,6-trimethylpyridine) perchlorate; 4 A molecular sieve; sodium hydride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(91)80023-G

upstream raw materials:

methyl 3,4-O-isopropylidene-2,6-di-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

(3aS,4R,6R,7R,7aS)-7-(4-Methoxy-benzyloxy)-4-(4-methoxy-benzyloxymethyl)-2,2-dimethyl-6-pent-4-enyloxy-tetrahydro-[1,3]dioxolo[4,5-c]pyran

methyl 3,4-O-isopropylidene-1-thio-β-D-galactopyranoside