(3aR,5R,5aS,8aS,8bR)-5-[(3R,4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-eth-(Z)-ylidene-3-methyl-hexahydro-4,5-dioxa-1-thia-naphthalen-3-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-[(3R,4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-eth-(Z)-ylidene-3-methyl-hexahydro-4,5-dioxa-1-thia-naphthalen-3-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran
• CAS No.: 243142-15-6
• Molecular Formula: C₄₄H₅₄O₁₁S
• Molecular Weight: 790.972

Synonyms:(3aR,5R,5aS,8aS,8bR)-5-[(3R,4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-eth-(Z)-ylidene-3-methyl-hexahydro-4,5-dioxa-1-thia-naphthalen-3-yloxymethyl]-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-[(3R,4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-eth-(Z)-ylidene-3-methyl-hexahydro-4,5-dioxa-1-thia-naphthalen-3-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran

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Technology Process of (3aR,5R,5aS,8aS,8bR)-5-[(3R,4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-eth-(Z)-ylidene-3-methyl-hexahydro-4,5-dioxa-1-thia-naphthalen-3-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran

There total 2 articles about (3aR,5R,5aS,8aS,8bR)-5-[(3R,4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-eth-(Z)-ylidene-3-methyl-hexahydro-4,5-dioxa-1-thia-naphthalen-3-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: 80.4%

3,4,6-tri-O-benzyl-1-O,2-S-[2-(1S-hydroxyethyl)-1-methyl-1,2-ethenediyl]-2-thio-α-D-glucopyranose (243142-18-9) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) → (3aR,5R,5aS,8aS,8bR)-5-[(3R,4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-eth-(Z)-ylidene-3-methyl-hexahydro-4,5-dioxa-1-thia-naphthalen-3-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran (243142-15-6)

Guidance literature:

With 4 A molecular sieve; trifluoroacetic acid; In dichloromethane; at 25 ℃; for 5.5h;

DOI:10.1002/(SICI)1099-0690(199908)1999:8<1869::AID-EJOC1869<3.0.CO;2-A

Reference yield:

1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-α-D-glucopyranose (152420-91-2) → (3aR,5R,5aS,8aS,8bR)-5-[(3R,4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-eth-(Z)-ylidene-3-methyl-hexahydro-4,5-dioxa-1-thia-naphthalen-3-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran (243142-15-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 48 percent / NaBH₄ / ethanol / 1 h

2: 80.4 percent / powdered 4 Angstroem molecular sieves; trifluoroacetic acid / CH₂Cl₂ / 5.5 h / 25 °C

With sodium tetrahydroborate; 4 A molecular sieve; trifluoroacetic acid; In ethanol; dichloromethane; 1: Hydrogenation / 2: Addition;

DOI:10.1002/(SICI)1099-0690(199908)1999:8<1869::AID-EJOC1869<3.0.CO;2-A

Reference yield:

(3aR,5R,5aS,8aS,8bR)-5-[(3R,4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-eth-(Z)-ylidene-3-methyl-hexahydro-4,5-dioxa-1-thia-naphthalen-3-yloxymethyl]-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran (243142-15-6) → 6-[2-S-(1'-acetyl-2'-methylethenyl)-3,4,6-tri-O-benzyl-2-thio-β-D-glucopyranosyl]-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside (243142-16-7)

Guidance literature:

With 4 A molecular sieve; toluene-4-sulfonic acid; In dichloromethane; at 25 ℃; for 7.5h;

DOI:10.1002/(SICI)1099-0690(199908)1999:8<1869::AID-EJOC1869<3.0.CO;2-A

upstream raw materials:

3,4,6-tri-O-benzyl-1-O,2-S-[2-(1S-hydroxyethyl)-1-methyl-1,2-ethenediyl]-2-thio-α-D-glucopyranose

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

1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-α-D-glucopyranose

Downstream raw materials:

6-[2-S-(1'-acetyl-2'-methylethenyl)-3,4,6-tri-O-benzyl-2-thio-β-D-glucopyranosyl]-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside

O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1[*]6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

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