(2S,3S,4R,5R,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2S,3S,4R,5R,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol
• CAS No.: 97576-68-6
• Molecular Formula: C₃₀H₃₄O₆
• Molecular Weight: 490.596
• Mol file: 97576-68-6.mol

Synonyms:(2S,3S,4R,5R,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol

Chemical Property of (2S,3S,4R,5R,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5R,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol

There total 14 articles about (2S,3S,4R,5R,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol 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: 98.0%

1-O-allyl-2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside (79317-18-3) → (2S,3S,4R,5R,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol (97576-68-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; at 20 ℃; for 16h;

DOI:10.1016/j.carres.2005.11.027

Reference yield: 94.0%

C37H38O7 → (2S,3S,4R,5R,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol (97576-68-6)

Guidance literature:

With methanol; sodium methylate; at 25 ℃; for 1h;

DOI:10.1039/c6sc04866h

Reference yield: 77.0%

exo-3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranoside + allyl alcohol (107-18-6) → (2S,3S,4R,5R,6R)-2-Allyloxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-3-ol (97576-68-6)

Guidance literature:

exo-3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranoside; allyl alcohol; With boron trifluoride diethyl etherate;

With sodium methylate; In methanol;

DOI:10.1021/ja409097c

upstream raw materials:

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

3,4,6-tri-O-benzyl-D-glucal

allyl alcohol

2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate

Downstream raw materials:

allyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

allyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-O-(3,6-di-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

allyl O-<3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl>-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside

allyl 3,4,6-tri-O-benzyl-2-O-<3,4,6-tri-O-benzyl-2-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-α-D-mannopyranosyl>-α-D-mannopyranoside