(3aR,5R,5aS,8aS,8bR)-5-[1-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-iodo-propoxymethyl]-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-[1-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-iodo-propoxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran
• CAS No.: 455929-01-8
• Molecular Formula: C₄₃H₅₅IO₁₁S
• Molecular Weight: 906.874

Synonyms:(3aR,5R,5aS,8aS,8bR)-5-[1-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-iodo-propoxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran

Chemical Property of (3aR,5R,5aS,8aS,8bR)-5-[1-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-iodo-propoxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran

Chemical Property:

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Technology Process of (3aR,5R,5aS,8aS,8bR)-5-[1-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-iodo-propoxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran

There total 3 articles about (3aR,5R,5aS,8aS,8bR)-5-[1-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-iodo-propoxymethyl]-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: 85.0%

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) + methyl 2-O-(prop-1-enyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (301645-94-3) → (3aR,5R,5aS,8aS,8bR)-5-[1-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-iodo-propoxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran (455929-01-8)

Guidance literature:

With N-iodo-succinimide; 4 A molecular sieve; In dichloromethane; at -40 - 20 ℃;

DOI:10.1002/1521-3765(20020603)8:11<2608::AID-CHEM2608>3.0.CO;2-4

Reference yield:

methyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (129163-10-6) → (3aR,5R,5aS,8aS,8bR)-5-[1-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-iodo-propoxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran (455929-01-8)

Guidance literature:

Multi-step reaction with 4 steps

1: MeONa / methanol

2: NaH / dimethylformamide

3: 99 percent / n-BuLi / (Ph₃P)3RhCl / tetrahydrofuran / Heating

4: N-iodosuccinimide; 4 Angstroem molecular sieves / acetonitrile / -40 - 20 °C

With N-iodo-succinimide; n-butyllithium; 4 A molecular sieve; sodium methylate; sodium hydride; Wilkinson's catalyst; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; acetonitrile; 1: Deacetylation / 2: Etherification / 3: Isomerization / 4: Addition;

DOI:10.1039/b004522p

Reference yield:

methyl 2-O-allyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside (301645-93-2) → (3aR,5R,5aS,8aS,8bR)-5-[1-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-methylsulfanyl-tetrahydro-pyran-3-yloxy)-2-iodo-propoxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran (455929-01-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / n-BuLi / (Ph₃P)3RhCl / tetrahydrofuran / Heating

2: N-iodosuccinimide; 4 Angstroem molecular sieves / acetonitrile / -40 - 20 °C

With N-iodo-succinimide; n-butyllithium; 4 A molecular sieve; Wilkinson's catalyst; In tetrahydrofuran; acetonitrile; 1: Isomerization / 2: Addition;

DOI:10.1039/b004522p

upstream raw materials:

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

methyl 2-O-(prop-1-enyl)-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

methyl 2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

methyl 2-O-allyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside

Downstream raw materials:

(3,4,6-tri-O-benzyI-β-D-mannopyranosyl)-(1→6)-1,2,3,4-di-O-isoprpopylidene-α-D-galactopyranoside

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