(3aS,4R,6S,7S,7aR)-7-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-6-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine

Base Information

• Chemical Name: (3aS,4R,6S,7S,7aR)-7-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-6-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine
• CAS No.: 352220-06-5
• Molecular Formula: C₆₇H₇₇NO₉Si
• Molecular Weight: 1068.44
• Mol file: 352220-06-5.mol

Synonyms:(3aS,4R,6S,7S,7aR)-7-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-6-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine

Chemical Property of (3aS,4R,6S,7S,7aR)-7-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-6-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4R,6S,7S,7aR)-7-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-6-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine

There total 6 articles about (3aS,4R,6S,7S,7aR)-7-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-6-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine 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: 72.0%

(R)-1-Benzyloxy-1-{(4R,5R)-5-[2-(tert-butyl-diphenyl-silanyloxy)-acetyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propan-2-one (352220-04-3) → (3aS,4R,6S,7S,7aR)-7-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-6-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine (352220-06-5)

Guidance literature:

With 4 A molecular sieve; ammonium formate; sodium cyanoborohydride; In methanol;

DOI:10.1039/b101598m

Reference yield:

benzyl bromide (100-39-0) → (3aS,4R,6S,7S,7aR)-7-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-6-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine (352220-06-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / AgOTf / CH₂Cl₂

2: NaBH₄ / ethanol

3: 72 percent / NaCNBH₃; NH₄HCO₂; molecular sieves 4 Angstroem / methanol

With sodium tetrahydroborate; 4 A molecular sieve; ammonium formate; silver trifluoromethanesulfonate; sodium cyanoborohydride; In methanol; ethanol; dichloromethane; 3: Swern oxidation;

DOI:10.1039/b101598m

Reference yield:

3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-2-deoxy-D-arabino-hex-1-enopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside (224324-96-3) → (3aS,4R,6S,7S,7aR)-7-Benzyloxy-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-6-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridine (352220-06-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / OsO₄; NMNO / acetone

2: 87 percent / AgOTf / CH₂Cl₂

3: NaBH₄ / ethanol

4: 72 percent / NaCNBH₃; NH₄HCO₂; molecular sieves 4 Angstroem / methanol

With sodium tetrahydroborate; osmium(VIII) oxide; bis-(2-chloro-ethyl)-methyl-amine oxide; 4 A molecular sieve; ammonium formate; silver trifluoromethanesulfonate; sodium cyanoborohydride; In methanol; ethanol; dichloromethane; acetone; 4: Swern oxidation;

DOI:10.1039/b101598m

upstream raw materials:

(R)-1-Benzyloxy-1-{(4R,5R)-5-[2-(tert-butyl-diphenyl-silanyloxy)-acetyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-3-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propan-2-one

benzyl bromide

3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-2-deoxy-D-arabino-hex-1-enopyranosyl 1-carba-2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside

Downstream raw materials:

[(3aS,4R,6S,7S,7aR)-7-Benzyloxy-2,2-dimethyl-6-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-hexahydro-[1,3]dioxolo[4,5-c]pyridin-4-yl]-methanol