(2R,3S,4S,5R,6R)-3,4,5-tri(benzyloxy)-6-[(benzyloxy)methyl]-5,6-dihydro-2-[3-[(4-methoxybenzyloxy)-methyl]-1,4-dithiin-2-yl]tetrahydro-2H-2-pyranol

Base Information

• Chemical Name: (2R,3S,4S,5R,6R)-3,4,5-tri(benzyloxy)-6-[(benzyloxy)methyl]-5,6-dihydro-2-[3-[(4-methoxybenzyloxy)-methyl]-1,4-dithiin-2-yl]tetrahydro-2H-2-pyranol
• CAS No.: 414858-56-3
• Molecular Formula: C₄₇H₅₀O₈S₂
• Molecular Weight: 807.041
• Mol file: 414858-56-3.mol

Synonyms:(2R,3S,4S,5R,6R)-3,4,5-tri(benzyloxy)-6-[(benzyloxy)methyl]-5,6-dihydro-2-[3-[(4-methoxybenzyloxy)-methyl]-1,4-dithiin-2-yl]tetrahydro-2H-2-pyranol

Chemical Property of (2R,3S,4S,5R,6R)-3,4,5-tri(benzyloxy)-6-[(benzyloxy)methyl]-5,6-dihydro-2-[3-[(4-methoxybenzyloxy)-methyl]-1,4-dithiin-2-yl]tetrahydro-2H-2-pyranol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R,6R)-3,4,5-tri(benzyloxy)-6-[(benzyloxy)methyl]-5,6-dihydro-2-[3-[(4-methoxybenzyloxy)-methyl]-1,4-dithiin-2-yl]tetrahydro-2H-2-pyranol

There total 1 articles about (2R,3S,4S,5R,6R)-3,4,5-tri(benzyloxy)-6-[(benzyloxy)methyl]-5,6-dihydro-2-[3-[(4-methoxybenzyloxy)-methyl]-1,4-dithiin-2-yl]tetrahydro-2H-2-pyranol 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: 87.0%

2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone (82598-88-7) + 1-[[O-(p-methoxybenzyl)-oxy]methyl]-5,6-dihydro-1,4-dithiin (199393-60-7) → (2R,3S,4S,5R,6R)-3,4,5-tri(benzyloxy)-6-[(benzyloxy)methyl]-5,6-dihydro-2-[3-[(4-methoxybenzyloxy)-methyl]-1,4-dithiin-2-yl]tetrahydro-2H-2-pyranol (414858-56-3)

Guidance literature:

1-[[O-(p-methoxybenzyl)-oxy]methyl]-5,6-dihydro-1,4-dithiin; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.666667h;

2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone; In tetrahydrofuran; at -78 ℃; for 3h;

DOI:10.1002/1099-0690(20022)2002:3<534::aid-ejoc534>3.0.co;2-r

Reference yield: 85.0%

(2R,3S,4S,5R,6R)-3,4,5-tri(benzyloxy)-6-[(benzyloxy)methyl]-5,6-dihydro-2-[3-[(4-methoxybenzyloxy)-methyl]-1,4-dithiin-2-yl]tetrahydro-2H-2-pyranol (414858-56-3) → C39H40O6S2 (414858-59-6)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/1099-0690(20022)2002:3<534::aid-ejoc534>3.0.co;2-r

Reference yield:

(2R,3S,4S,5R,6R)-3,4,5-tri(benzyloxy)-6-[(benzyloxy)methyl]-5,6-dihydro-2-[3-[(4-methoxybenzyloxy)-methyl]-1,4-dithiin-2-yl]tetrahydro-2H-2-pyranol (414858-56-3) → (5R,7R,8R,9S,10S)-8,9,10-tri(benzyloxy)-7-[(benzyloxy)methyl]-1,6-dioxaspiro[4,5]dec-3-ene

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / 20 °C

2: 70 percent / Raney-Ni / acetic acid / 0.58 h / 20 °C

With boron trifluoride diethyl etherate; nickel; In dichloromethane; acetic acid;

DOI:10.1002/1099-0690(20022)2002:3<534::aid-ejoc534>3.0.co;2-r

upstream raw materials:

2,3,4,6-tetra-O-benzyl-D-mannono-1,5-lactone

1-[[O-(p-methoxybenzyl)-oxy]methyl]-5,6-dihydro-1,4-dithiin

Downstream raw materials:

C₃₉H₄₀O₆S₂